NPASS Compound

Structure

NPC40234 OpenBabel07101718322D 69 72 0 0 1 0 0 0 0 0999 V2000 -0.8827 5.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1030 -6.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4283 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4044 1.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0486 1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4777 0.1430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1876 -2.5643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7507 5.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5651 4.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9434 -3.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 3.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1035 -2.8094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0323 -4.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3526 -2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2814 -3.4916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3259 3.4256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8254 -4.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9830 -3.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6679 -4.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8254 -2.6909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0547 -4.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6943 -4.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4262 -4.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1405 -4.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9397 -1.2952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8475 0.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 -5.9656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1201 1.1604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7994 -0.5543 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4415 -2.5321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9830 -4.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6679 -3.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0984 -5.6231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2980 -4.1500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0331 0.9509 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0287 -1.6363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6423 -4.4226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2723 2.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5356 -4.3514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7154 0.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9074 0.2111 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3755 -1.3381 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6796 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1651 0.5117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5423 -0.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6659 -2.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0653 -5.5161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0816 -3.5546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9361 0.2647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0867 1.9222 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1491 -5.4104 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6391 -3.2390 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8087 -0.1550 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1115 -0.4597 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2152 -2.5911 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9450 -5.1009 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5104 -2.6909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4043 2.0150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1024 -3.5608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5298 0.3260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7690 1.8294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3185 -5.6345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3507 1.0437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2932 -0.1754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6295 -2.1330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3300 -6.4522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0100 -3.8450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8291 1.2316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 55 1 0 0 0 0 8 9 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 30 2 0 0 0 0 15 30 1 0 0 0 0 16 38 1 0 0 0 0 17 19 1 0 0 0 0 17 31 2 0 0 0 0 18 20 2 0 0 0 0 18 31 1 0 0 0 0 19 32 2 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 22 39 1 0 0 0 0 23 27 1 0 0 0 0 24 31 1 0 0 0 0 25 30 1 0 0 0 0 26 40 1 0 0 0 0 29 6 1 1 0 0 0 29 42 1 0 0 0 0 29 69 1 0 0 0 0 32 57 1 0 0 0 0 33 21 1 6 0 0 0 33 47 1 0 0 0 0 33 51 1 0 0 0 0 34 24 1 6 0 0 0 34 43 1 0 0 0 0 34 52 1 0 0 0 0 35 26 1 6 0 0 0 35 44 1 0 0 0 0 35 50 1 0 0 0 0 36 25 1 6 0 0 0 36 45 1 0 0 0 0 36 55 1 0 0 0 0 37 23 1 6 0 0 0 37 48 1 0 0 0 0 37 56 1 0 0 0 0 38 50 2 3 0 0 0 38 58 1 0 0 0 0 39 56 1 0 0 0 0 39 59 1 1 0 0 0 40 60 2 0 0 0 0 40 61 1 0 0 0 0 41 28 1 6 0 0 0 41 49 1 0 0 0 0 41 53 1 0 0 0 0 42 46 1 0 0 0 0 42 54 1 1 0 0 0 43 51 2 3 0 0 0 43 62 1 0 0 0 0 44 54 2 3 0 0 0 44 63 1 0 0 0 0 45 53 2 3 0 0 0 45 64 1 0 0 0 0 46 52 2 3 0 0 0 46 65 1 0 0 0 0 47 56 1 0 0 0 0 47 66 2 0 0 0 0 48 55 1 0 0 0 0 48 67 2 0 0 0 0 49 68 2 0 0 0 0 49 69 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	963.5
Volume:	973.537
LogP:	3.158
LogD:	1.158
LogS:	-2.65
# Rotatable Bonds:	18
TPSA:	293.67
# H-Bond Aceptor:	20
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	6.729
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.888
MDCK Permeability:	3.876739719999023e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.857
20% Bioavailability (F20%):	0.775
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	62.45216751098633%
Volume Distribution (VD):	0.339
Pgp-substrate:	14.919647216796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.208
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	5.208
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.456
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.429
Carcinogencity:	0.315
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.372

Download Data

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

Natural Product: NPC40234

Natural Product ID:	NPC40234
*Common Name:**	Cyanopeptolin 963A
IUPAC Name:	(3S)-4-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-21-hydroxy-15-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-2-(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-(hexanoylamino)-4-oxobutanoic acid
Synonyms:
Standard InCHIKey:	NGPDQWFWZNXVLZ-AYGLBTBXSA-N
Standard InCHI:	InChI=1S/C49H69N7O13/c1-8-9-11-16-38(58)50-35(26-40(60)61)44(63)54-42-29(6)69-49(68)41(28(4)5)53-45(64)36(25-30-14-12-10-13-15-30)55(7)48(67)37(23-27(2)3)56-39(59)22-21-33(47(56)66)51-43(62)34(52-46(42)65)24-31-17-19-32(57)20-18-31/h10,12-15,17-20,27-29,33-37,39,41-42,57,59H,8-9,11,16,21-26H2,1-7H3,(H,50,58)(H,51,62)(H,52,65)(H,53,64)(H,54,63)(H,60,61)/t29-,33+,34+,35+,36+,37+,39-,41+,42+/m1/s1
SMILES:	CCCCCC(=N[C@@H](CC(=O)O)C(=N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N=C([C@H](Cc2ccccc2)N(C)C(=O)[C@H](CC(C)C)N2[C@@H](CC[C@@H](C2=O)N=C([C@H](Cc2ccc(cc2)O)N=C1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255705
PubChem CID:	11193939
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
NPO33223	microcystis pcc 7806	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15497957]

☑ 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
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	900.0	nM	PMID[468888]
NPT2	Others	Unspecified		IC50	=	900.0	nM	PMID[468889]

☑ 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 NPC40234 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	190
0.1-0.2	967
0.2-0.3	3926
0.3-0.4	13097
0.4-0.5	10764
0.5-0.6	12302
0.6-0.7	1008
0.7-0.8	343
0.8-0.85	51
0.85-0.9	24
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9613	High Similarity	NPC294516
0.9613	High Similarity	NPC107938
0.9557	High Similarity	NPC476227
0.9497	High Similarity	NPC50016
0.943	High Similarity	NPC230611
0.9371	High Similarity	NPC273755
0.9371	High Similarity	NPC137627
0.9371	High Similarity	NPC306804
0.9313	High Similarity	NPC473402
0.9313	High Similarity	NPC155506
0.9313	High Similarity	NPC279871
0.9313	High Similarity	NPC159767
0.9313	High Similarity	NPC473354
0.9245	High Similarity	NPC475204
0.9245	High Similarity	NPC475123
0.9141	High Similarity	NPC194671
0.9141	High Similarity	NPC269750
0.9141	High Similarity	NPC45037
0.9125	High Similarity	NPC46009
0.9107	High Similarity	NPC240130
0.9107	High Similarity	NPC61332
0.903	High Similarity	NPC476321
0.8976	High Similarity	NPC471526
0.8922	High Similarity	NPC294951
0.8841	High Similarity	NPC471165
0.8841	High Similarity	NPC26108
0.881	High Similarity	NPC471048
0.881	High Similarity	NPC471050
0.881	High Similarity	NPC471049
0.878	High Similarity	NPC248670
0.869	High Similarity	NPC473404
0.8663	High Similarity	NPC163961
0.8663	High Similarity	NPC473305
0.8621	High Similarity	NPC65714
0.8613	High Similarity	NPC473378
0.8613	High Similarity	NPC473407
0.8589	High Similarity	NPC61004
0.8523	High Similarity	NPC473371
0.8514	High Similarity	NPC302715
0.8503	High Similarity	NPC158277
0.8475	Intermediate Similarity	NPC471592
0.8431	Intermediate Similarity	NPC163392
0.8431	Intermediate Similarity	NPC239762
0.8428	Intermediate Similarity	NPC262166
0.8418	Intermediate Similarity	NPC473491
0.8397	Intermediate Similarity	NPC81026
0.8391	Intermediate Similarity	NPC102959
0.8383	Intermediate Similarity	NPC89831
0.8375	Intermediate Similarity	NPC39431
0.8343	Intermediate Similarity	NPC60516
0.8333	Intermediate Similarity	NPC266741
0.8313	Intermediate Similarity	NPC473341
0.8313	Intermediate Similarity	NPC302597
0.8303	Intermediate Similarity	NPC63931
0.825	Intermediate Similarity	NPC233702
0.8228	Intermediate Similarity	NPC16188
0.8193	Intermediate Similarity	NPC472923
0.8171	Intermediate Similarity	NPC244336
0.8141	Intermediate Similarity	NPC476989
0.809	Intermediate Similarity	NPC248822
0.8089	Intermediate Similarity	NPC91953
0.8086	Intermediate Similarity	NPC56685
0.8086	Intermediate Similarity	NPC202198
0.8046	Intermediate Similarity	NPC477637
0.8036	Intermediate Similarity	NPC254700
0.8035	Intermediate Similarity	NPC475421
0.8033	Intermediate Similarity	NPC477551
0.8025	Intermediate Similarity	NPC197921
0.8024	Intermediate Similarity	NPC471051
0.8024	Intermediate Similarity	NPC471053
0.8024	Intermediate Similarity	NPC471052
0.8022	Intermediate Similarity	NPC477552
0.8022	Intermediate Similarity	NPC477550
0.8012	Intermediate Similarity	NPC469243
0.8	Intermediate Similarity	NPC274198
0.8	Intermediate Similarity	NPC473693
0.8	Intermediate Similarity	NPC198254
0.8	Intermediate Similarity	NPC471568
0.7988	Intermediate Similarity	NPC244509
0.7988	Intermediate Similarity	NPC476268
0.7988	Intermediate Similarity	NPC328649
0.7976	Intermediate Similarity	NPC223207
0.7975	Intermediate Similarity	NPC261934
0.7975	Intermediate Similarity	NPC5194
0.7975	Intermediate Similarity	NPC469360
0.7965	Intermediate Similarity	NPC136797
0.7964	Intermediate Similarity	NPC241794
0.7953	Intermediate Similarity	NPC328494
0.7941	Intermediate Similarity	NPC186617
0.7935	Intermediate Similarity	NPC469443
0.7929	Intermediate Similarity	NPC304074
0.7929	Intermediate Similarity	NPC290755
0.7929	Intermediate Similarity	NPC471771
0.7921	Intermediate Similarity	NPC94862
0.7919	Intermediate Similarity	NPC196243
0.791	Intermediate Similarity	NPC315542
0.7904	Intermediate Similarity	NPC471527
0.7904	Intermediate Similarity	NPC475544
0.7901	Intermediate Similarity	NPC328763
0.7898	Intermediate Similarity	NPC167763
0.7898	Intermediate Similarity	NPC470903
0.7898	Intermediate Similarity	NPC470112
0.7895	Intermediate Similarity	NPC276506
0.7895	Intermediate Similarity	NPC196091
0.7882	Intermediate Similarity	NPC141957
0.7882	Intermediate Similarity	NPC473502
0.7857	Intermediate Similarity	NPC477638
0.7857	Intermediate Similarity	NPC477632
0.7834	Intermediate Similarity	NPC127741
0.7834	Intermediate Similarity	NPC6570
0.7833	Intermediate Similarity	NPC174122
0.7833	Intermediate Similarity	NPC64140
0.7809	Intermediate Similarity	NPC299806
0.7806	Intermediate Similarity	NPC257390
0.7802	Intermediate Similarity	NPC314083
0.7778	Intermediate Similarity	NPC234069
0.7771	Intermediate Similarity	NPC473580
0.7764	Intermediate Similarity	NPC209509
0.7742	Intermediate Similarity	NPC473450
0.773	Intermediate Similarity	NPC323662
0.7716	Intermediate Similarity	NPC314358
0.7701	Intermediate Similarity	NPC475532
0.7684	Intermediate Similarity	NPC220060
0.7679	Intermediate Similarity	NPC326349
0.7679	Intermediate Similarity	NPC323336
0.7674	Intermediate Similarity	NPC209463
0.7667	Intermediate Similarity	NPC276120
0.7657	Intermediate Similarity	NPC17698
0.7657	Intermediate Similarity	NPC165285
0.7654	Intermediate Similarity	NPC316008
0.7654	Intermediate Similarity	NPC313867
0.7651	Intermediate Similarity	NPC122590
0.7644	Intermediate Similarity	NPC469444
0.764	Intermediate Similarity	NPC161069
0.7634	Intermediate Similarity	NPC50548
0.7633	Intermediate Similarity	NPC319320
0.7633	Intermediate Similarity	NPC62104
0.7633	Intermediate Similarity	NPC1390
0.7633	Intermediate Similarity	NPC287757
0.763	Intermediate Similarity	NPC280022
0.7627	Intermediate Similarity	NPC119652
0.7627	Intermediate Similarity	NPC97526
0.7611	Intermediate Similarity	NPC138083
0.761	Intermediate Similarity	NPC471265
0.761	Intermediate Similarity	NPC471264
0.7602	Intermediate Similarity	NPC133470
0.7602	Intermediate Similarity	NPC191863
0.7602	Intermediate Similarity	NPC289776
0.7596	Intermediate Similarity	NPC477526
0.7593	Intermediate Similarity	NPC315283
0.7593	Intermediate Similarity	NPC314388
0.7584	Intermediate Similarity	NPC153554
0.7584	Intermediate Similarity	NPC32064
0.7581	Intermediate Similarity	NPC144314
0.758	Intermediate Similarity	NPC326966
0.7562	Intermediate Similarity	NPC313694
0.7562	Intermediate Similarity	NPC242159
0.7557	Intermediate Similarity	NPC164608
0.7554	Intermediate Similarity	NPC477631
0.7553	Intermediate Similarity	NPC242728
0.7541	Intermediate Similarity	NPC477636
0.7532	Intermediate Similarity	NPC244866
0.7529	Intermediate Similarity	NPC129486
0.7527	Intermediate Similarity	NPC149962
0.7527	Intermediate Similarity	NPC4910
0.7526	Intermediate Similarity	NPC469445
0.75	Intermediate Similarity	NPC469666
0.75	Intermediate Similarity	NPC194699
0.75	Intermediate Similarity	NPC123859
0.75	Intermediate Similarity	NPC219350
0.7485	Intermediate Similarity	NPC476978
0.7473	Intermediate Similarity	NPC59827
0.7473	Intermediate Similarity	NPC184933
0.7471	Intermediate Similarity	NPC212699
0.7471	Intermediate Similarity	NPC297145
0.7471	Intermediate Similarity	NPC207675
0.7471	Intermediate Similarity	NPC56635
0.7471	Intermediate Similarity	NPC197743
0.747	Intermediate Similarity	NPC132771
0.747	Intermediate Similarity	NPC2501
0.7469	Intermediate Similarity	NPC263493
0.7469	Intermediate Similarity	NPC269398
0.7458	Intermediate Similarity	NPC477462
0.7457	Intermediate Similarity	NPC5719
0.7457	Intermediate Similarity	NPC210377
0.7457	Intermediate Similarity	NPC217804
0.7457	Intermediate Similarity	NPC22883
0.7455	Intermediate Similarity	NPC135121
0.7455	Intermediate Similarity	NPC138775
0.7453	Intermediate Similarity	NPC92784
0.7453	Intermediate Similarity	NPC470884
0.7453	Intermediate Similarity	NPC178662
0.7453	Intermediate Similarity	NPC476133
0.7453	Intermediate Similarity	NPC98424
0.7439	Intermediate Similarity	NPC201244
0.7439	Intermediate Similarity	NPC5620
0.7439	Intermediate Similarity	NPC477217
0.7433	Intermediate Similarity	NPC477639
0.7433	Intermediate Similarity	NPC329295
0.7432	Intermediate Similarity	NPC329731

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 NPC40234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	384
0.2-0.3	813
0.3-0.4	1825
0.4-0.5	2978
0.5-0.6	2385
0.6-0.7	612
0.7-0.8	30
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
0.8221	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8303	Discontinued
0.7688	Intermediate Similarity	NPD7608	Discontinued
0.7651	Intermediate Similarity	NPD7131	Phase 3
0.764	Intermediate Similarity	NPD7978	Discontinued
0.7594	Intermediate Similarity	NPD7810	Phase 3
0.7594	Intermediate Similarity	NPD7811	Phase 3
0.7561	Intermediate Similarity	NPD8323	Discontinued
0.7529	Intermediate Similarity	NPD8019	Approved
0.7529	Intermediate Similarity	NPD7484	Phase 3
0.7529	Intermediate Similarity	NPD7485	Phase 3
0.7516	Intermediate Similarity	NPD3136	Phase 2
0.744	Intermediate Similarity	NPD7523	Phase 3
0.7427	Intermediate Similarity	NPD7495	Discontinued
0.7375	Intermediate Similarity	NPD6346	Approved
0.7356	Intermediate Similarity	NPD8031	Discontinued
0.7288	Intermediate Similarity	NPD4652	Approved
0.7284	Intermediate Similarity	NPD8173	Phase 2
0.7284	Intermediate Similarity	NPD8172	Phase 2
0.7278	Intermediate Similarity	NPD7303	Discontinued
0.7278	Intermediate Similarity	NPD7613	Discontinued
0.7273	Intermediate Similarity	NPD6681	Discovery
0.7256	Intermediate Similarity	NPD7450	Phase 2
0.7244	Intermediate Similarity	NPD4659	Approved
0.7243	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6851	Approved
0.7228	Intermediate Similarity	NPD6853	Approved
0.7228	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3125	Approved
0.7193	Intermediate Similarity	NPD8315	Phase 1
0.7159	Intermediate Similarity	NPD2098	Approved
0.7152	Intermediate Similarity	NPD4103	Phase 2
0.7152	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD8417	Discontinued
0.7108	Intermediate Similarity	NPD8076	Discontinued
0.7099	Intermediate Similarity	NPD5745	Approved
0.7091	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3400	Discontinued
0.7056	Intermediate Similarity	NPD5137	Approved
0.7055	Intermediate Similarity	NPD8416	Discontinued
0.7045	Intermediate Similarity	NPD2097	Approved
0.7039	Intermediate Similarity	NPD2888	Approved
0.7039	Intermediate Similarity	NPD2017	Approved
0.7039	Intermediate Similarity	NPD2890	Approved
0.7039	Intermediate Similarity	NPD2889	Approved
0.7022	Intermediate Similarity	NPD8245	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8643	Discontinued
0.7011	Intermediate Similarity	NPD6297	Approved
0.699	Remote Similarity	NPD8356	Approved
0.6987	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5746	Approved
0.6964	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8265	Approved
0.6949	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1330	Phase 2
0.6933	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8351	Phase 2
0.6901	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7972	Discontinued
0.6886	Remote Similarity	NPD1753	Discontinued
0.6882	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8430	Approved
0.6855	Remote Similarity	NPD2584	Suspended
0.6845	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD8161	Suspended
0.6828	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6852	Discontinued
0.6824	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7280	Phase 3
0.6809	Remote Similarity	NPD7281	Phase 3
0.6798	Remote Similarity	NPD5773	Approved
0.6798	Remote Similarity	NPD5772	Approved
0.6791	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7451	Discontinued
0.6789	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7565	Approved
0.6784	Remote Similarity	NPD6676	Phase 2
0.6782	Remote Similarity	NPD6390	Discontinued
0.6774	Remote Similarity	NPD5485	Approved
0.6774	Remote Similarity	NPD5484	Approved
0.6768	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8162	Phase 2
0.6766	Remote Similarity	NPD6073	Approved
0.6766	Remote Similarity	NPD2568	Approved
0.676	Remote Similarity	NPD5967	Approved
0.6754	Remote Similarity	NPD8025	Phase 2
0.675	Remote Similarity	NPD2562	Approved
0.675	Remote Similarity	NPD2561	Approved
0.6744	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3553	Approved
0.6726	Remote Similarity	NPD3554	Approved
0.6726	Remote Similarity	NPD6295	Approved
0.6726	Remote Similarity	NPD6294	Approved
0.6726	Remote Similarity	NPD6901	Phase 3
0.6726	Remote Similarity	NPD3555	Approved
0.6726	Remote Similarity	NPD3552	Approved
0.672	Remote Similarity	NPD5312	Approved
0.672	Remote Similarity	NPD5313	Approved
0.6718	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4620	Approved
0.6707	Remote Similarity	NPD5203	Approved
0.6707	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5201	Approved
0.6707	Remote Similarity	NPD4617	Approved
0.6705	Remote Similarity	NPD6666	Approved
0.6705	Remote Similarity	NPD6667	Approved
0.6703	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2904	Discontinued
0.6702	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5481	Discontinued
0.6686	Remote Similarity	NPD4731	Phase 3
0.6685	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5557	Phase 1
0.6667	Remote Similarity	NPD4435	Approved
0.6667	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7737	Approved
0.6667	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7738	Approved
0.6667	Remote Similarity	NPD5723	Approved
0.6647	Remote Similarity	NPD1725	Approved
0.6647	Remote Similarity	NPD3692	Discontinued
0.6647	Remote Similarity	NPD5120	Approved
0.6647	Remote Similarity	NPD5119	Approved
0.6647	Remote Similarity	NPD5121	Approved
0.6647	Remote Similarity	NPD5296	Approved
0.6646	Remote Similarity	NPD4175	Approved
0.6646	Remote Similarity	NPD4177	Approved
0.6633	Remote Similarity	NPD6255	Approved
0.6633	Remote Similarity	NPD6256	Approved
0.6633	Remote Similarity	NPD6254	Approved
0.6632	Remote Similarity	NPD7617	Discontinued
0.6631	Remote Similarity	NPD6042	Phase 2
0.6631	Remote Similarity	NPD42	Phase 2
0.6629	Remote Similarity	NPD3536	Discontinued
0.6627	Remote Similarity	NPD5688	Approved
0.6627	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5689	Approved
0.6615	Remote Similarity	NPD4434	Approved
0.6612	Remote Similarity	NPD5823	Approved
0.6611	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4677	Discontinued
0.6598	Remote Similarity	NPD6505	Approved
0.6598	Remote Similarity	NPD6504	Approved
0.6596	Remote Similarity	NPD5190	Phase 2
0.6593	Remote Similarity	NPD5218	Approved
0.6593	Remote Similarity	NPD5219	Approved
0.6591	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6405	Approved
0.6587	Remote Similarity	NPD7715	Approved
0.6587	Remote Similarity	NPD6407	Approved
0.6587	Remote Similarity	NPD7714	Approved
0.6585	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6253	Approved
0.6582	Remote Similarity	NPD6312	Discontinued
0.6578	Remote Similarity	NPD3909	Discontinued
0.6576	Remote Similarity	NPD6107	Approved
0.6575	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6088	Approved
0.6568	Remote Similarity	NPD3052	Approved
0.6568	Remote Similarity	NPD5314	Approved
0.6568	Remote Similarity	NPD3054	Approved
0.6568	Remote Similarity	NPD5725	Approved
0.6566	Remote Similarity	NPD6039	Approved
0.6561	Remote Similarity	NPD5445	Approved
0.6557	Remote Similarity	NPD6862	Phase 2
0.6556	Remote Similarity	NPD7011	Discontinued
0.6556	Remote Similarity	NPD5355	Approved
0.6556	Remote Similarity	NPD5356	Approved
0.655	Remote Similarity	NPD6032	Approved
0.6548	Remote Similarity	NPD6623	Phase 3
0.6543	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4603	Phase 2
0.6541	Remote Similarity	NPD5304	Approved
0.6541	Remote Similarity	NPD5303	Approved
0.6534	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4619	Approved
0.6527	Remote Similarity	NPD4621	Approved
0.6527	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2159	Approved
0.6524	Remote Similarity	NPD2627	Approved
0.6524	Remote Similarity	NPD2160	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