NPASS Compound

Structure

NPC63040 OpenBabel07101719122D 68 70 0 0 1 0 0 0 0 0999 V2000 -5.7373 0.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7026 -8.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0929 -0.8631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0226 -7.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -1.9188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0060 -4.9867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4728 -0.4050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9523 -8.3324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6891 -6.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9017 -5.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7614 -6.6304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5271 -7.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1865 -4.7334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0462 -5.9721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5807 -6.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7611 -6.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4304 -6.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6598 -8.0602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8285 -3.7069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8418 -1.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1506 -1.1018 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1123 -7.3736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1434 -2.6518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2588 -5.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4480 -6.2118 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7578 -7.8134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9008 -3.9971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8418 -2.4301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2617 -6.6237 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8861 -2.0371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5254 -3.4021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3619 -6.7557 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0236 -6.9950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4619 -3.1298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1846 -4.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7283 -7.7599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8480 -5.9139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9200 -1.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2610 -9.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0748 -8.9380 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3146 -10.4402 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6063 -9.0307 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1578 -5.2841 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8224 -7.5489 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.7652 -2.4520 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8418 -2.4301 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.0343 -4.9599 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6289 -7.3941 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8707 -5.8662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3458 -7.6918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2451 -2.5541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.8881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2306 -4.1261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9409 -8.7084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7583 -6.2547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8664 -0.9596 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9720 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9720 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0394 -1.5883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3672 -1.9441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0114 -3.2719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9715 -2.1428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6836 -2.9161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2.5254 -2.4301 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 6 48 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 16 17 1 0 0 0 0 17 29 1 0 0 0 0 18 43 1 0 0 0 0 19 24 1 0 0 0 0 20 64 1 0 0 0 0 21 3 1 1 0 0 0 22 4 1 6 0 0 0 23 5 1 6 0 0 0 23 31 1 0 0 0 0 23 65 1 0 0 0 0 25 15 1 1 0 0 0 25 33 1 0 0 0 0 25 44 1 0 0 0 0 26 16 1 1 0 0 0 26 37 1 0 0 0 0 26 45 1 0 0 0 0 27 19 1 1 0 0 0 27 34 1 0 0 0 0 27 48 1 0 0 0 0 28 20 1 1 0 0 0 28 35 1 0 0 0 0 28 66 1 0 0 0 0 29 49 1 0 0 0 0 29 50 1 6 0 0 0 30 21 1 1 0 0 0 30 39 1 0 0 0 0 30 46 1 0 0 0 0 31 36 1 0 0 0 0 31 47 1 6 0 0 0 32 22 1 1 0 0 0 32 38 1 0 0 0 0 32 49 1 0 0 0 0 33 45 2 3 0 0 0 33 51 1 0 0 0 0 34 46 2 3 0 0 0 34 52 1 0 0 0 0 35 47 2 3 0 0 0 35 53 1 0 0 0 0 36 44 2 3 0 0 0 36 54 1 0 0 0 0 37 49 1 0 0 0 0 37 55 2 0 0 0 0 38 48 1 0 0 0 0 38 56 2 0 0 0 0 39 57 2 0 0 0 0 39 65 1 0 0 0 0 40 41 2 0 0 0 0 40 42 1 0 0 0 0 40 43 1 0 0 0 0 58 67 1 0 0 0 0 59 67 2 0 0 0 0 60 67 2 0 0 0 0 61 68 1 0 0 0 0 62 68 2 0 0 0 0 63 68 2 0 0 0 0 64 67 1 0 0 0 0 66 68 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1005.38
Volume:	931.148
LogP:	-1.343
LogD:	-0.505
LogS:	-0.212
# Rotatable Bonds:	19
TPSA:	392.65
# H-Bond Aceptor:	26
# H-Bond Donor:	11
# Rings:	3
# Heavy Atoms:	28

MedChem Properties

QED Drug-Likeness Score:	0.026
Synthetic Accessibility Score:	7.059
Fsp3:	0.65
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.496
MDCK Permeability:	3.3268792321905494e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	69.04814910888672%
Volume Distribution (VD):	0.402
Pgp-substrate:	19.986570358276367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.954
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.772
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.349
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.404
Carcinogencity:	0.75
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.951

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC63040

Natural Product ID:	NPC63040
*Common Name:**	Cyanopeptolin Ss
IUPAC Name:	[(2R)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-2,8-bis[(2S)-butan-2-yl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-1-oxo-3-sulfooxypropan-2-yl] hydrogen sulfate
Synonyms:	cyanopeptolin SS
Standard InCHIKey:	KBCHLKMABDZVKD-LKAQEJCWSA-N
Standard InCHI:	InChI=1S/C40H63N9O17S2/c1-7-21(3)30-39(57)65-23(5)31(47-35(53)28(66-68(61,62)63)20-64-67(58,59)60)36(54)44-25(15-12-18-43-40(41)42)33(51)45-26-16-17-29(50)49(37(26)55)32(22(4)8-2)38(56)48(6)27(34(52)46-30)19-24-13-10-9-11-14-24/h9-11,13-14,21-23,25-32,50H,7-8,12,15-20H2,1-6H3,(H,44,54)(H,45,51)(H,46,52)(H,47,53)(H4,41,42,43)(H,58,59,60)(H,61,62,63)/t21-,22-,23+,25-,26-,27-,28+,29+,30-,31-,32-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H]([C@H](CC)C)N2[C@H](O)CC[C@@H](C2=O)N=C([C@@H](N=C([C@H]([C@H](OC1=O)C)N=C([C@H](OS(=O)(=O)O)COS(=O)(=O)O)O)O)CCCNC(=N)N)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076839
PubChem CID:	46881046
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	n.a.	Germany	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	Israeli fishpond water bloom	n.a.	n.a.	PMID[20028081]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	n.a.	Varanasi, India	n.a.	PMID[23777401]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO32761	microcystis sp.	Species	Microcystaceae	Bacteria	n.a.	Tel Aviv Safari in Israel	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	2900.0	nM	PMID[506863]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	45200.0	nM	PMID[506863]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC63040 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	851
0.2-0.3	4707
0.3-0.4	24047
0.4-0.5	10599
0.5-0.6	1680
0.6-0.7	398
0.7-0.8	234
0.8-0.85	18
0.85-0.9	5
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC15068
0.9868	High Similarity	NPC217804
0.9868	High Similarity	NPC22883
0.9868	High Similarity	NPC5719
0.9868	High Similarity	NPC210377
0.9603	High Similarity	NPC62104
0.9603	High Similarity	NPC1390
0.9038	High Similarity	NPC471527
0.8988	High Similarity	NPC60516
0.8929	High Similarity	NPC102959
0.8613	High Similarity	NPC302715
0.8543	High Similarity	NPC239762
0.8543	High Similarity	NPC163392
0.8418	Intermediate Similarity	NPC473341
0.8353	Intermediate Similarity	NPC473404
0.8344	Intermediate Similarity	NPC471052
0.8344	Intermediate Similarity	NPC471051
0.8344	Intermediate Similarity	NPC471053
0.8251	Intermediate Similarity	NPC220060
0.8228	Intermediate Similarity	NPC2501
0.8187	Intermediate Similarity	NPC122590
0.8125	Intermediate Similarity	NPC300443
0.8098	Intermediate Similarity	NPC197743
0.8098	Intermediate Similarity	NPC297145
0.8075	Intermediate Similarity	NPC469445
0.8025	Intermediate Similarity	NPC52748
0.8023	Intermediate Similarity	NPC61332
0.8023	Intermediate Similarity	NPC240130
0.7989	Intermediate Similarity	NPC25539
0.7923	Intermediate Similarity	NPC469443
0.7923	Intermediate Similarity	NPC477551
0.7914	Intermediate Similarity	NPC469444
0.7912	Intermediate Similarity	NPC477550
0.7912	Intermediate Similarity	NPC477552
0.7884	Intermediate Similarity	NPC277306
0.7884	Intermediate Similarity	NPC469442
0.7882	Intermediate Similarity	NPC46009
0.7879	Intermediate Similarity	NPC324850
0.7862	Intermediate Similarity	NPC315266
0.7844	Intermediate Similarity	NPC73655
0.784	Intermediate Similarity	NPC7817
0.784	Intermediate Similarity	NPC475168
0.7831	Intermediate Similarity	NPC24617
0.7829	Intermediate Similarity	NPC476321
0.7826	Intermediate Similarity	NPC471820
0.7826	Intermediate Similarity	NPC471821
0.7821	Intermediate Similarity	NPC68865
0.7821	Intermediate Similarity	NPC127741
0.7803	Intermediate Similarity	NPC50016
0.7791	Intermediate Similarity	NPC273755
0.7784	Intermediate Similarity	NPC471526
0.7784	Intermediate Similarity	NPC114806
0.7771	Intermediate Similarity	NPC132636
0.774	Intermediate Similarity	NPC471050
0.774	Intermediate Similarity	NPC471048
0.774	Intermediate Similarity	NPC471049
0.7736	Intermediate Similarity	NPC176226
0.7722	Intermediate Similarity	NPC476259
0.7714	Intermediate Similarity	NPC45037
0.7697	Intermediate Similarity	NPC470902
0.7688	Intermediate Similarity	NPC476978
0.7674	Intermediate Similarity	NPC475204
0.7674	Intermediate Similarity	NPC475123
0.7673	Intermediate Similarity	NPC168113
0.7672	Intermediate Similarity	NPC194699
0.7672	Intermediate Similarity	NPC219350
0.7643	Intermediate Similarity	NPC314835
0.7625	Intermediate Similarity	NPC197682
0.7624	Intermediate Similarity	NPC163961
0.7624	Intermediate Similarity	NPC473305
0.761	Intermediate Similarity	NPC268841
0.761	Intermediate Similarity	NPC46098
0.761	Intermediate Similarity	NPC307357
0.7593	Intermediate Similarity	NPC262077
0.7586	Intermediate Similarity	NPC306804
0.7546	Intermediate Similarity	NPC135121
0.7543	Intermediate Similarity	NPC473354
0.7543	Intermediate Similarity	NPC477462
0.7532	Intermediate Similarity	NPC319766
0.7531	Intermediate Similarity	NPC201244
0.7531	Intermediate Similarity	NPC477217
0.7531	Intermediate Similarity	NPC5620
0.7516	Intermediate Similarity	NPC161069
0.7516	Intermediate Similarity	NPC77905
0.7486	Intermediate Similarity	NPC473378
0.7486	Intermediate Similarity	NPC473407
0.7485	Intermediate Similarity	NPC314114
0.7484	Intermediate Similarity	NPC471264
0.7484	Intermediate Similarity	NPC471265
0.7471	Intermediate Similarity	NPC198254
0.7471	Intermediate Similarity	NPC274198
0.7459	Intermediate Similarity	NPC477638
0.7459	Intermediate Similarity	NPC477632
0.7457	Intermediate Similarity	NPC294516
0.7457	Intermediate Similarity	NPC107938
0.7447	Intermediate Similarity	NPC473450
0.7429	Intermediate Similarity	NPC230611
0.7423	Intermediate Similarity	NPC209509
0.7418	Intermediate Similarity	NPC94862
0.7416	Intermediate Similarity	NPC194671
0.7416	Intermediate Similarity	NPC269750
0.7389	Intermediate Similarity	NPC130309
0.7386	Intermediate Similarity	NPC137627
0.7378	Intermediate Similarity	NPC314358
0.7371	Intermediate Similarity	NPC276506
0.7371	Intermediate Similarity	NPC40234
0.7365	Intermediate Similarity	NPC162104
0.7358	Intermediate Similarity	NPC141050
0.7351	Intermediate Similarity	NPC477631
0.7349	Intermediate Similarity	NPC129666
0.7348	Intermediate Similarity	NPC294951
0.7346	Intermediate Similarity	NPC263493
0.7346	Intermediate Similarity	NPC269398
0.7345	Intermediate Similarity	NPC26108
0.7345	Intermediate Similarity	NPC473402
0.7345	Intermediate Similarity	NPC471165
0.7345	Intermediate Similarity	NPC279871
0.7337	Intermediate Similarity	NPC477636
0.7333	Intermediate Similarity	NPC138775
0.7333	Intermediate Similarity	NPC311658
0.7329	Intermediate Similarity	NPC470884
0.7329	Intermediate Similarity	NPC178662
0.7329	Intermediate Similarity	NPC98424
0.7329	Intermediate Similarity	NPC92784
0.7329	Intermediate Similarity	NPC476133
0.7317	Intermediate Similarity	NPC316008
0.7317	Intermediate Similarity	NPC313867
0.7314	Intermediate Similarity	NPC280022
0.7314	Intermediate Similarity	NPC473000
0.7303	Intermediate Similarity	NPC196243
0.7301	Intermediate Similarity	NPC139326
0.7273	Intermediate Similarity	NPC6975
0.7273	Intermediate Similarity	NPC46427
0.7267	Intermediate Similarity	NPC469901
0.7256	Intermediate Similarity	NPC314388
0.7256	Intermediate Similarity	NPC315283
0.7255	Intermediate Similarity	NPC71684
0.7247	Intermediate Similarity	NPC476227
0.7247	Intermediate Similarity	NPC159767
0.7247	Intermediate Similarity	NPC155506
0.7239	Intermediate Similarity	NPC469426
0.7239	Intermediate Similarity	NPC469427
0.7229	Intermediate Similarity	NPC329761
0.7229	Intermediate Similarity	NPC225648
0.7229	Intermediate Similarity	NPC145113
0.7208	Intermediate Similarity	NPC252878
0.7204	Intermediate Similarity	NPC248822
0.7191	Intermediate Similarity	NPC248670
0.7188	Intermediate Similarity	NPC287401
0.7186	Intermediate Similarity	NPC105717
0.7182	Intermediate Similarity	NPC153554
0.7171	Intermediate Similarity	NPC237420
0.7152	Intermediate Similarity	NPC111428
0.7143	Intermediate Similarity	NPC63931
0.7143	Intermediate Similarity	NPC477639
0.7143	Intermediate Similarity	NPC202521
0.7134	Intermediate Similarity	NPC477937
0.7128	Intermediate Similarity	NPC65714
0.7127	Intermediate Similarity	NPC119652
0.7127	Intermediate Similarity	NPC97526
0.7119	Intermediate Similarity	NPC129486
0.7118	Intermediate Similarity	NPC286551
0.7111	Intermediate Similarity	NPC469900
0.711	Intermediate Similarity	NPC469898
0.7095	Intermediate Similarity	NPC475532
0.7088	Intermediate Similarity	NPC472999
0.7083	Intermediate Similarity	NPC240848
0.7078	Intermediate Similarity	NPC476990
0.7069	Intermediate Similarity	NPC469243
0.7059	Intermediate Similarity	NPC314992
0.7059	Intermediate Similarity	NPC470546
0.7056	Intermediate Similarity	NPC165285
0.7056	Intermediate Similarity	NPC17698
0.7053	Intermediate Similarity	NPC473371
0.7035	Intermediate Similarity	NPC473580
0.7035	Intermediate Similarity	NPC469903
0.7019	Intermediate Similarity	NPC246079
0.7016	Intermediate Similarity	NPC471592
0.6993	Remote Similarity	NPC169328
0.6993	Remote Similarity	NPC470545
0.6979	Remote Similarity	NPC323662
0.6971	Remote Similarity	NPC475544
0.6971	Remote Similarity	NPC469902
0.6968	Remote Similarity	NPC477061
0.6968	Remote Similarity	NPC45777
0.6962	Remote Similarity	NPC101719
0.6961	Remote Similarity	NPC317362
0.6961	Remote Similarity	NPC318930
0.6957	Remote Similarity	NPC477637
0.6957	Remote Similarity	NPC255447
0.6949	Remote Similarity	NPC223207
0.6948	Remote Similarity	NPC310467
0.6943	Remote Similarity	NPC35996
0.6928	Remote Similarity	NPC470544
0.6928	Remote Similarity	NPC2265
0.6919	Remote Similarity	NPC478005
0.6911	Remote Similarity	NPC80514
0.691	Remote Similarity	NPC290755
0.691	Remote Similarity	NPC304074
0.691	Remote Similarity	NPC471771

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC63040 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	296
0.2-0.3	678
0.3-0.4	2397
0.4-0.5	4241
0.5-0.6	1221
0.6-0.7	197
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8194	Intermediate Similarity	NPD8076	Discontinued
0.7771	Intermediate Similarity	NPD6901	Phase 3
0.7595	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8303	Discontinued
0.7358	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8173	Phase 2
0.7267	Intermediate Similarity	NPD6073	Approved
0.7267	Intermediate Similarity	NPD8172	Phase 2
0.7262	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4177	Approved
0.7261	Intermediate Similarity	NPD4175	Approved
0.725	Intermediate Similarity	NPD5296	Approved
0.7246	Intermediate Similarity	NPD6088	Approved
0.7233	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8323	Discontinued
0.7176	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5725	Approved
0.7152	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6681	Discovery
0.7151	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6852	Discontinued
0.7089	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5747	Discontinued
0.7076	Intermediate Similarity	NPD7836	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2217	Approved
0.7059	Intermediate Similarity	NPD2218	Phase 2
0.7037	Intermediate Similarity	NPD4153	Approved
0.7012	Intermediate Similarity	NPD6295	Approved
0.7012	Intermediate Similarity	NPD6294	Approved
0.7006	Intermediate Similarity	NPD4677	Discontinued
0.6994	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3073	Approved
0.6943	Remote Similarity	NPD3072	Approved
0.6943	Remote Similarity	NPD2584	Suspended
0.6943	Remote Similarity	NPD3071	Approved
0.6933	Remote Similarity	NPD6623	Phase 3
0.6918	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8019	Approved
0.6905	Remote Similarity	NPD5264	Approved
0.6905	Remote Similarity	NPD5265	Approved
0.6897	Remote Similarity	NPD8417	Discontinued
0.6897	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5263	Approved
0.6879	Remote Similarity	NPD4761	Approved
0.6879	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4762	Approved
0.6875	Remote Similarity	NPD4151	Approved
0.6867	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7342	Discontinued
0.6855	Remote Similarity	NPD5367	Discontinued
0.6852	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6646	Discontinued
0.6818	Remote Similarity	NPD7495	Discontinued
0.679	Remote Similarity	NPD4676	Approved
0.679	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3040	Approved
0.6727	Remote Similarity	NPD8416	Discontinued
0.6724	Remote Similarity	NPD7523	Phase 3
0.6707	Remote Similarity	NPD5581	Approved
0.6704	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3908	Approved
0.6685	Remote Similarity	NPD4557	Approved
0.6667	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7484	Phase 3
0.6648	Remote Similarity	NPD7485	Phase 3
0.6647	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5614	Approved
0.6647	Remote Similarity	NPD5613	Approved
0.6627	Remote Similarity	NPD8265	Approved
0.6626	Remote Similarity	NPD3626	Phase 3
0.6607	Remote Similarity	NPD4126	Approved
0.6606	Remote Similarity	NPD1330	Phase 2
0.6606	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8315	Phase 1
0.659	Remote Similarity	NPD3519	Discontinued
0.6588	Remote Similarity	NPD4152	Approved
0.6585	Remote Similarity	NPD4125	Approved
0.6578	Remote Similarity	NPD5774	Approved
0.6578	Remote Similarity	NPD5775	Approved
0.6573	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4794	Discontinued
0.6545	Remote Similarity	NPD4738	Phase 2
0.6543	Remote Similarity	NPD3125	Approved
0.6527	Remote Similarity	NPD5323	Approved
0.6514	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4566	Approved
0.65	Remote Similarity	NPD4567	Approved
0.6497	Remote Similarity	NPD4647	Approved
0.6497	Remote Similarity	NPD4648	Approved
0.6497	Remote Similarity	NPD4646	Approved
0.6488	Remote Similarity	NPD8643	Discontinued
0.6477	Remote Similarity	NPD7613	Discontinued
0.6444	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7508	Discontinued
0.6433	Remote Similarity	NPD1348	Approved
0.6432	Remote Similarity	NPD7608	Discontinued
0.6424	Remote Similarity	NPD7828	Discontinued
0.6417	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4214	Discontinued
0.6411	Remote Similarity	NPD8271	Discontinued
0.6407	Remote Similarity	NPD5299	Approved
0.6402	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2088	Approved
0.6395	Remote Similarity	NPD7978	Discontinued
0.6395	Remote Similarity	NPD2087	Approved
0.6395	Remote Similarity	NPD7720	Phase 2
0.6389	Remote Similarity	NPD7105	Phase 1
0.6386	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5230	Approved
0.6384	Remote Similarity	NPD5638	Approved
0.6384	Remote Similarity	NPD5229	Approved
0.6384	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6864	Phase 2
0.6374	Remote Similarity	NPD6865	Phase 2
0.6368	Remote Similarity	NPD7973	Discontinued
0.6364	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3588	Discontinued
0.6364	Remote Similarity	NPD3987	Approved
0.6364	Remote Similarity	NPD3988	Approved
0.6364	Remote Similarity	NPD8124	Phase 3
0.6352	Remote Similarity	NPD7522	Discontinued
0.6343	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8351	Phase 2
0.6337	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8162	Phase 2
0.6333	Remote Similarity	NPD2891	Approved
0.6331	Remote Similarity	NPD5272	Discontinued
0.6328	Remote Similarity	NPD5942	Approved
0.6328	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5941	Approved
0.6321	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7908	Discontinued
0.6303	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6304	Approved
0.629	Remote Similarity	NPD6839	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6303	Approved
0.6286	Remote Similarity	NPD1967	Approved
0.6286	Remote Similarity	NPD1968	Approved
0.6286	Remote Similarity	NPD6676	Phase 2
0.6284	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD7744	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7965	Phase 2
0.6263	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD8119	Discontinued
0.6256	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8075	Discontinued
0.625	Remote Similarity	NPD3136	Phase 2
0.6243	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7512	Approved
0.6243	Remote Similarity	NPD7511	Approved
0.6237	Remote Similarity	NPD6853	Approved
0.6237	Remote Similarity	NPD6851	Approved
0.6216	Remote Similarity	NPD8031	Discontinued
0.6215	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4091	Approved
0.6207	Remote Similarity	NPD2022	Approved
0.6203	Remote Similarity	NPD7890	Discontinued
0.6196	Remote Similarity	NPD7600	Phase 2
0.6196	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD8169	Discontinued
0.6193	Remote Similarity	NPD7617	Discontinued
0.619	Remote Similarity	NPD2613	Approved
0.6188	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD3480	Approved
0.618	Remote Similarity	NPD2013	Approved
0.618	Remote Similarity	NPD2014	Approved
0.618	Remote Similarity	NPD2016	Approved
0.6178	Remote Similarity	NPD3996	Approved
0.6178	Remote Similarity	NPD3992	Approved
0.6178	Remote Similarity	NPD3991	Approved
0.6178	Remote Similarity	NPD3994	Approved
0.6178	Remote Similarity	NPD3993	Approved
0.6178	Remote Similarity	NPD3995	Approved
0.6178	Remote Similarity	NPD4092	Approved
0.6176	Remote Similarity	NPD2566	Approved
0.6176	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3089	Approved
0.6176	Remote Similarity	NPD4746	Phase 3
0.6176	Remote Similarity	NPD2574	Discontinued
0.6176	Remote Similarity	NPD3616	Approved
0.6176	Remote Similarity	NPD2571	Approved
0.6176	Remote Similarity	NPD3088	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data