NPASS Compound

Structure

NPC473305 OpenBabel07101719172D 81 85 0 0 1 0 0 0 0 0999 V2000 9.1692 -12.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9447 -4.9985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3045 -4.5832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9346 -4.0120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7671 -7.8073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5674 -7.2107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7452 -8.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1938 -12.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1182 -12.4819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -12.3211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4971 -11.7278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4242 -11.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 -10.8129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0039 -4.0120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4692 -4.8580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9014 -4.1077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2865 -3.6026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0039 -5.7040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4924 -3.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9577 -4.0120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1930 -3.1754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5781 -2.6703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4924 -6.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2702 -11.0612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9537 -10.2641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3649 -6.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1457 -9.7373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8883 -2.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0047 -5.2643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4230 -4.8580 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.8431 -8.1245 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.4924 -4.8580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8032 -10.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9481 -4.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4692 -3.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5313 -2.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6595 -11.5724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4692 -6.5500 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8443 -11.8056 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0265 -6.9048 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1093 -9.5765 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.3999 -3.1660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.1332 -10.0145 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.7649 -6.2113 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.0039 -9.0880 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.9346 -5.7040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7649 -11.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9577 -7.3960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8443 -6.3705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8883 -4.0120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8431 -10.0516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0265 -11.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1093 -8.5996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6595 -6.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3999 -4.8580 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.3782 -10.9107 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.9577 -5.7040 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7913 -12.0455 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7913 -6.1306 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.9808 -9.0880 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4265 -7.6757 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4265 -10.5004 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.9577 -2.3200 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 4.8230 -1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4230 -3.1660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4230 -6.5500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0047 -12.9118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9346 -7.3960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4519 -5.4759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8652 -4.0120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7671 -10.3688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3649 -11.9901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1457 -8.4388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1938 -5.7859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4230 -0.4971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4461 -1.4740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4230 -2.4509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9838 -9.0491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3999 -1.4740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3782 -7.2653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4230 -1.4740 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 61 1 0 0 0 0 7 78 1 0 0 0 0 8 37 2 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 33 2 0 0 0 0 13 33 1 0 0 0 0 14 19 1 0 0 0 0 14 32 2 0 0 0 0 15 20 2 0 0 0 0 15 32 1 0 0 0 0 16 21 1 0 0 0 0 16 34 2 0 0 0 0 17 22 2 0 0 0 0 17 34 1 0 0 0 0 18 23 1 0 0 0 0 18 32 1 0 0 0 0 19 35 2 0 0 0 0 20 35 1 0 0 0 0 21 36 2 0 0 0 0 22 36 1 0 0 0 0 23 38 1 0 0 0 0 24 25 1 0 0 0 0 24 39 1 0 0 0 0 25 43 1 0 0 0 0 26 34 1 0 0 0 0 26 40 1 0 0 0 0 27 33 1 0 0 0 0 27 41 1 0 0 0 0 28 42 1 0 0 0 0 28 79 1 0 0 0 0 29 44 1 0 0 0 0 30 46 1 0 0 0 0 30 55 1 0 0 0 0 31 45 1 0 0 0 0 31 80 1 0 0 0 0 35 63 1 0 0 0 0 36 64 1 0 0 0 0 37 47 1 0 0 0 0 37 56 1 0 0 0 0 38 48 1 0 0 0 0 38 57 1 0 0 0 0 39 52 1 0 0 0 0 39 58 1 0 0 0 0 40 49 1 0 0 0 0 40 61 1 0 0 0 0 41 53 1 0 0 0 0 41 62 1 0 0 0 0 42 50 1 0 0 0 0 42 65 1 0 0 0 0 43 62 1 0 0 0 0 43 78 1 0 0 0 0 44 54 1 0 0 0 0 44 59 1 0 0 0 0 45 51 1 0 0 0 0 45 60 1 0 0 0 0 46 57 2 0 0 0 0 46 66 1 0 0 0 0 47 58 2 0 0 0 0 47 67 1 0 0 0 0 48 60 2 0 0 0 0 48 68 1 0 0 0 0 49 59 2 0 0 0 0 49 69 1 0 0 0 0 50 55 2 0 0 0 0 50 70 1 0 0 0 0 51 56 2 0 0 0 0 51 71 1 0 0 0 0 52 62 1 0 0 0 0 52 72 2 0 0 0 0 53 61 1 0 0 0 0 53 73 2 0 0 0 0 54 74 2 0 0 0 0 54 80 1 0 0 0 0 75 81 1 0 0 0 0 76 81 2 0 0 0 0 77 81 2 0 0 0 0 79 81 1 0 0 0 0 M CHG 1 63 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	1149.45
Volume:	1113.054
LogP:	0.522
LogD:	0.484
LogS:	-1.809
# Rotatable Bonds:	20
TPSA:	384.85
# H-Bond Aceptor:	26
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.021
Synthetic Accessibility Score:	7.571
Fsp3:	0.463
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:	-6.761
MDCK Permeability:	7.1015115281625185e-06
Pgp-inhibitor:	0.696
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.576
20% Bioavailability (F20%):	0.754
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	64.0710678100586%
Volume Distribution (VD):	0.421
Pgp-substrate:	23.616426467895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.029
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.749
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.013
Half-life (T1/2):	0.478

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.293
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.588
Carcinogencity:	0.235
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC473305

Natural Product ID:	NPC473305
*Common Name:**	Lyngbyastatin 6
IUPAC Name:	sodium;[(2R)-3-[[(2S)-1-[[(2S)-1-[[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-15-ethylidene-5-[(4-hydroxyphenyl)methyl]-21-methoxy-4,11-dimethyl-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]-4-(4-hydroxyphenyl)-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-hydroxy-3-oxopropyl] sulfate
Synonyms:	Lyngbyastatin 6
Standard InCHIKey:	ORIYPXBBMZLHAY-AODXAMECSA-M
Standard InCHI:	InChI=1S/C54H70N8O18S.Na/c1-8-37-47(67)58-39-24-25-43(78-7)62(52(39)72)41(27-33-12-10-9-11-13-33)53(73)61(6)40(26-34-16-21-36(64)22-17-34)49(69)59-44(29(2)3)54(74)80-31(5)45(51(71)56-37)60-48(68)38(23-18-32-14-19-35(63)20-15-32)57-46(66)30(4)55-50(70)42(65)28-79-81(75,76)77;/h8-17,19-22,29-31,38-45,63-65H,18,23-28H2,1-7H3,(H,55,70)(H,56,71)(H,57,66)(H,58,67)(H,59,69)(H,60,68)(H,75,76,77);/q;+1/p-1/b37-8-;/t30-,31+,38-,39-,40-,41-,42+,43+,44-,45-;/m0./s1
SMILES:	CO[C@@H]1CC[C@H]2C(=O)N1[C@@H](Cc1ccccc1)C(=O)N(C)[C@@H](Cc1ccc(cc1)O)C(=N[C@@H](C(C)C)C(=O)O[C@@H]([C@@H](C(=N/C(=CC)/C(=N2)O)O)N=C([C@@H](N=C([C@@H](N=C([C@@H](COS(=O)(=O)O)O)O)C)O)CCc1ccc(cc1)[O-])O)C)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399106
PubChem CID:	23672420
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
NPO32763	lyngbya spp.	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[17910513]

☑ 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	=	3.3	nM	PMID[547828]
NPT2	Others	Unspecified		IC50	=	2500.0	nM	PMID[547828]

☑ 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 NPC473305 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	218
0.1-0.2	1126
0.2-0.3	4382
0.3-0.4	12810
0.4-0.5	13263
0.5-0.6	9800
0.6-0.7	789
0.7-0.8	244
0.8-0.85	29
0.85-0.9	24
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC163961
0.9702	High Similarity	NPC294951
0.9586	High Similarity	NPC471049
0.9586	High Similarity	NPC471048
0.9586	High Similarity	NPC471050
0.9527	High Similarity	NPC471526
0.9353	High Similarity	NPC476321
0.9286	High Similarity	NPC279871
0.9148	High Similarity	NPC473378
0.9148	High Similarity	NPC473407
0.9123	High Similarity	NPC194671
0.9123	High Similarity	NPC45037
0.9123	High Similarity	NPC269750
0.9059	High Similarity	NPC155506
0.9059	High Similarity	NPC159767
0.9059	High Similarity	NPC473354
0.9053	High Similarity	NPC230611
0.8947	High Similarity	NPC473402
0.8895	High Similarity	NPC50016
0.8889	High Similarity	NPC273755
0.8889	High Similarity	NPC137627
0.8889	High Similarity	NPC306804
0.8833	High Similarity	NPC302715
0.8765	High Similarity	NPC107938
0.8765	High Similarity	NPC294516
0.8728	High Similarity	NPC476227
0.8728	High Similarity	NPC26108
0.8698	High Similarity	NPC471051
0.8698	High Similarity	NPC471053
0.8698	High Similarity	NPC471052
0.8663	High Similarity	NPC40234
0.8611	High Similarity	NPC102959
0.8564	High Similarity	NPC60516
0.8486	Intermediate Similarity	NPC471592
0.8457	Intermediate Similarity	NPC248670
0.8448	Intermediate Similarity	NPC475123
0.8448	Intermediate Similarity	NPC475204
0.8448	Intermediate Similarity	NPC46009
0.8324	Intermediate Similarity	NPC65714
0.8305	Intermediate Similarity	NPC471165
0.8305	Intermediate Similarity	NPC158277
0.8261	Intermediate Similarity	NPC61332
0.8261	Intermediate Similarity	NPC240130
0.8235	Intermediate Similarity	NPC473371
0.8192	Intermediate Similarity	NPC89831
0.815	Intermediate Similarity	NPC471527
0.8114	Intermediate Similarity	NPC63931
0.8077	Intermediate Similarity	NPC473404
0.8053	Intermediate Similarity	NPC323662
0.7953	Intermediate Similarity	NPC233702
0.7937	Intermediate Similarity	NPC328763
0.7908	Intermediate Similarity	NPC220060
0.7876	Intermediate Similarity	NPC477551
0.7872	Intermediate Similarity	NPC174122
0.7872	Intermediate Similarity	NPC64140
0.7865	Intermediate Similarity	NPC477550
0.7865	Intermediate Similarity	NPC477552
0.7857	Intermediate Similarity	NPC196243
0.7819	Intermediate Similarity	NPC234069
0.7766	Intermediate Similarity	NPC94862
0.7765	Intermediate Similarity	NPC471771
0.7765	Intermediate Similarity	NPC304074
0.7765	Intermediate Similarity	NPC290755
0.775	Intermediate Similarity	NPC469445
0.7735	Intermediate Similarity	NPC196091
0.7722	Intermediate Similarity	NPC302597
0.7722	Intermediate Similarity	NPC328649
0.7722	Intermediate Similarity	NPC141957
0.7719	Intermediate Similarity	NPC16188
0.7709	Intermediate Similarity	NPC223207
0.7705	Intermediate Similarity	NPC136797
0.7705	Intermediate Similarity	NPC477462
0.7701	Intermediate Similarity	NPC262166
0.7701	Intermediate Similarity	NPC202198
0.7692	Intermediate Similarity	NPC469443
0.7688	Intermediate Similarity	NPC469444
0.768	Intermediate Similarity	NPC50548
0.7679	Intermediate Similarity	NPC239762
0.7679	Intermediate Similarity	NPC163392
0.7667	Intermediate Similarity	NPC61004
0.7661	Intermediate Similarity	NPC81026
0.766	Intermediate Similarity	NPC315542
0.766	Intermediate Similarity	NPC138083
0.7637	Intermediate Similarity	NPC274198
0.7637	Intermediate Similarity	NPC276506
0.7637	Intermediate Similarity	NPC198254
0.7634	Intermediate Similarity	NPC32064
0.7629	Intermediate Similarity	NPC144314
0.7624	Intermediate Similarity	NPC63040
0.7619	Intermediate Similarity	NPC276120
0.7611	Intermediate Similarity	NPC210377
0.7611	Intermediate Similarity	NPC22883
0.7611	Intermediate Similarity	NPC5719
0.7611	Intermediate Similarity	NPC217804
0.7602	Intermediate Similarity	NPC266741
0.7602	Intermediate Similarity	NPC242728
0.76	Intermediate Similarity	NPC122590
0.76	Intermediate Similarity	NPC478005
0.76	Intermediate Similarity	NPC473341
0.7596	Intermediate Similarity	NPC328494
0.7586	Intermediate Similarity	NPC473491
0.7581	Intermediate Similarity	NPC475421
0.7577	Intermediate Similarity	NPC149962
0.7569	Intermediate Similarity	NPC15068
0.7557	Intermediate Similarity	NPC39431
0.7552	Intermediate Similarity	NPC248822
0.7542	Intermediate Similarity	NPC475544
0.7542	Intermediate Similarity	NPC469243
0.7541	Intermediate Similarity	NPC473693
0.7541	Intermediate Similarity	NPC471568
0.7536	Intermediate Similarity	NPC478007
0.7528	Intermediate Similarity	NPC56635
0.7527	Intermediate Similarity	NPC209463
0.7514	Intermediate Similarity	NPC476268
0.7514	Intermediate Similarity	NPC472923
0.7514	Intermediate Similarity	NPC164608
0.75	Intermediate Similarity	NPC326027
0.75	Intermediate Similarity	NPC25539
0.75	Intermediate Similarity	NPC477637
0.7488	Intermediate Similarity	NPC469442
0.7488	Intermediate Similarity	NPC277306
0.7488	Intermediate Similarity	NPC326333
0.7487	Intermediate Similarity	NPC119652
0.7487	Intermediate Similarity	NPC97526
0.7486	Intermediate Similarity	NPC7817
0.7486	Intermediate Similarity	NPC280022
0.7486	Intermediate Similarity	NPC244336
0.7486	Intermediate Similarity	NPC475168
0.7486	Intermediate Similarity	NPC186617
0.7474	Intermediate Similarity	NPC314083
0.7473	Intermediate Similarity	NPC254700
0.7464	Intermediate Similarity	NPC478008
0.7462	Intermediate Similarity	NPC123859
0.746	Intermediate Similarity	NPC470903
0.746	Intermediate Similarity	NPC470112
0.746	Intermediate Similarity	NPC167763
0.7459	Intermediate Similarity	NPC191863
0.7459	Intermediate Similarity	NPC133470
0.7459	Intermediate Similarity	NPC289776
0.7456	Intermediate Similarity	NPC127741
0.7456	Intermediate Similarity	NPC6570
0.7429	Intermediate Similarity	NPC2501
0.7427	Intermediate Similarity	NPC476989
0.7409	Intermediate Similarity	NPC29531
0.7403	Intermediate Similarity	NPC241794
0.7401	Intermediate Similarity	NPC5194
0.7401	Intermediate Similarity	NPC261934
0.7389	Intermediate Similarity	NPC62104
0.7389	Intermediate Similarity	NPC1390
0.7384	Intermediate Similarity	NPC91953
0.7382	Intermediate Similarity	NPC299806
0.7381	Intermediate Similarity	NPC244866
0.7371	Intermediate Similarity	NPC477526
0.736	Intermediate Similarity	NPC470902
0.7354	Intermediate Similarity	NPC153554
0.735	Intermediate Similarity	NPC311357
0.7347	Intermediate Similarity	NPC477638
0.7347	Intermediate Similarity	NPC477632
0.7333	Intermediate Similarity	NPC197743
0.7333	Intermediate Similarity	NPC297145
0.7326	Intermediate Similarity	NPC197921
0.7321	Intermediate Similarity	NPC257390
0.7318	Intermediate Similarity	NPC473580
0.7318	Intermediate Similarity	NPC244509
0.7314	Intermediate Similarity	NPC135121
0.7306	Intermediate Similarity	NPC4910
0.7303	Intermediate Similarity	NPC56685
0.7299	Intermediate Similarity	NPC477217
0.7299	Intermediate Similarity	NPC201244
0.7291	Intermediate Similarity	NPC194699
0.7291	Intermediate Similarity	NPC219350
0.7283	Intermediate Similarity	NPC469360
0.7273	Intermediate Similarity	NPC475532
0.7259	Intermediate Similarity	NPC471563
0.7259	Intermediate Similarity	NPC59827
0.7259	Intermediate Similarity	NPC184933
0.7257	Intermediate Similarity	NPC262077
0.725	Intermediate Similarity	NPC473450
0.7243	Intermediate Similarity	NPC473502
0.7241	Intermediate Similarity	NPC52748
0.7234	Intermediate Similarity	NPC165285
0.7234	Intermediate Similarity	NPC17698
0.7216	Intermediate Similarity	NPC329731
0.7198	Intermediate Similarity	NPC319320
0.7198	Intermediate Similarity	NPC287757
0.7184	Intermediate Similarity	NPC161069
0.7175	Intermediate Similarity	NPC9373
0.715	Intermediate Similarity	NPC477527
0.7143	Intermediate Similarity	NPC476978
0.7136	Intermediate Similarity	NPC477639
0.7135	Intermediate Similarity	NPC245974
0.7118	Intermediate Similarity	NPC45191
0.7112	Intermediate Similarity	NPC129486
0.711	Intermediate Similarity	NPC242159
0.711	Intermediate Similarity	NPC313694
0.7102	Intermediate Similarity	NPC209509
0.7083	Intermediate Similarity	NPC475564
0.7083	Intermediate Similarity	NPC170302
0.7083	Intermediate Similarity	NPC475409
0.7079	Intermediate Similarity	NPC471820

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 NPC473305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	460
0.2-0.3	774
0.3-0.4	1889
0.4-0.5	3090
0.5-0.6	2489
0.6-0.7	309
0.7-0.8	6
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
0.7528	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7608	Discontinued
0.7414	Intermediate Similarity	NPD8323	Discontinued
0.7389	Intermediate Similarity	NPD8019	Approved
0.7303	Intermediate Similarity	NPD7131	Phase 3
0.7286	Intermediate Similarity	NPD7811	Phase 3
0.7286	Intermediate Similarity	NPD7810	Phase 3
0.7189	Intermediate Similarity	NPD8303	Discontinued
0.7056	Intermediate Similarity	NPD8356	Approved
0.7029	Intermediate Similarity	NPD7450	Phase 2
0.7026	Intermediate Similarity	NPD6853	Approved
0.7026	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6851	Approved
0.7011	Intermediate Similarity	NPD7495	Discontinued
0.701	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8430	Approved
0.6989	Remote Similarity	NPD7978	Discontinued
0.6931	Remote Similarity	NPD7484	Phase 3
0.6931	Remote Similarity	NPD7485	Phase 3
0.6902	Remote Similarity	NPD8417	Discontinued
0.6869	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7565	Approved
0.686	Remote Similarity	NPD3136	Phase 2
0.6856	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6297	Approved
0.6816	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7303	Discontinued
0.6772	Remote Similarity	NPD8031	Discontinued
0.6771	Remote Similarity	NPD5137	Approved
0.6761	Remote Similarity	NPD8173	Phase 2
0.6761	Remote Similarity	NPD8172	Phase 2
0.676	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8025	Phase 2
0.6743	Remote Similarity	NPD6346	Approved
0.6739	Remote Similarity	NPD7523	Phase 3
0.6735	Remote Similarity	NPD5445	Approved
0.6703	Remote Similarity	NPD8315	Phase 1
0.6685	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD2888	Approved
0.6667	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8161	Suspended
0.6667	Remote Similarity	NPD2017	Approved
0.6667	Remote Similarity	NPD3125	Approved
0.6667	Remote Similarity	NPD2889	Approved
0.6667	Remote Similarity	NPD2890	Approved
0.6649	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7617	Discontinued
0.6617	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5823	Approved
0.6612	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4659	Approved
0.6597	Remote Similarity	NPD2098	Approved
0.6596	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7613	Discontinued
0.6592	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7715	Approved
0.6591	Remote Similarity	NPD7714	Approved
0.6575	Remote Similarity	NPD6681	Discovery
0.6566	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5119	Approved
0.6554	Remote Similarity	NPD5120	Approved
0.6554	Remote Similarity	NPD5121	Approved
0.6546	Remote Similarity	NPD4652	Approved
0.6531	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7972	Discontinued
0.6526	Remote Similarity	NPD7585	Approved
0.6514	Remote Similarity	NPD4620	Approved
0.6514	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4617	Approved
0.6514	Remote Similarity	NPD5201	Approved
0.6514	Remote Similarity	NPD5203	Approved
0.651	Remote Similarity	NPD8070	Approved
0.6505	Remote Similarity	NPD6390	Discontinued
0.6503	Remote Similarity	NPD5481	Discontinued
0.6503	Remote Similarity	NPD6676	Phase 2
0.6497	Remote Similarity	NPD5745	Approved
0.6492	Remote Similarity	NPD5967	Approved
0.6492	Remote Similarity	NPD7737	Approved
0.6492	Remote Similarity	NPD7738	Approved
0.6492	Remote Similarity	NPD2097	Approved
0.648	Remote Similarity	NPD6073	Approved
0.6479	Remote Similarity	NPD7583	Approved
0.6474	Remote Similarity	NPD5356	Approved
0.6474	Remote Similarity	NPD5355	Approved
0.6471	Remote Similarity	NPD7861	Discontinued
0.6468	Remote Similarity	NPD8149	Discontinued
0.6468	Remote Similarity	NPD7281	Phase 3
0.6468	Remote Similarity	NPD7280	Phase 3
0.6458	Remote Similarity	NPD8351	Phase 2
0.6453	Remote Similarity	NPD2584	Suspended
0.6448	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD8162	Phase 2
0.6444	Remote Similarity	NPD6295	Approved
0.6444	Remote Similarity	NPD6294	Approved
0.6441	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD1330	Phase 2
0.644	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4103	Phase 2
0.6432	Remote Similarity	NPD5484	Approved
0.6432	Remote Similarity	NPD5485	Approved
0.6432	Remote Similarity	NPD5190	Phase 2
0.6425	Remote Similarity	NPD5218	Approved
0.6425	Remote Similarity	NPD555	Phase 2
0.6425	Remote Similarity	NPD5219	Approved
0.6422	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6677	Suspended
0.6409	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD3879	Approved
0.6402	Remote Similarity	NPD3455	Phase 2
0.6402	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7451	Discontinued
0.6398	Remote Similarity	NPD6254	Approved
0.6398	Remote Similarity	NPD6256	Approved
0.6398	Remote Similarity	NPD6255	Approved
0.6396	Remote Similarity	NPD6796	Discontinued
0.6392	Remote Similarity	NPD6862	Phase 2
0.6389	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7011	Discontinued
0.6384	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD4738	Phase 2
0.6384	Remote Similarity	NPD5746	Approved
0.6382	Remote Similarity	NPD5313	Approved
0.6382	Remote Similarity	NPD4603	Phase 2
0.6382	Remote Similarity	NPD5312	Approved
0.6369	Remote Similarity	NPD5296	Approved
0.6369	Remote Similarity	NPD8265	Approved
0.6368	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6863	Phase 2
0.6368	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6502	Phase 2
0.6364	Remote Similarity	NPD4177	Approved
0.6364	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4175	Approved
0.6359	Remote Similarity	NPD6505	Approved
0.6359	Remote Similarity	NPD6504	Approved
0.6359	Remote Similarity	NPD3878	Approved
0.6355	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6852	Discontinued
0.6351	Remote Similarity	NPD6253	Approved
0.6348	Remote Similarity	NPD4619	Approved
0.6348	Remote Similarity	NPD4621	Approved
0.6346	Remote Similarity	NPD6312	Discontinued
0.6345	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4435	Approved
0.634	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7110	Phase 1
0.6333	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7570	Approved
0.6329	Remote Similarity	NPD7569	Approved
0.6324	Remote Similarity	NPD6967	Phase 2
0.6322	Remote Similarity	NPD4677	Discontinued
0.6321	Remote Similarity	NPD7600	Phase 2
0.6319	Remote Similarity	NPD1753	Discontinued
0.6318	Remote Similarity	NPD8463	Approved
0.6318	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD259	Phase 1
0.6311	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6088	Approved
0.6306	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD5035	Approved
0.63	Remote Similarity	NPD3965	Phase 1
0.6298	Remote Similarity	NPD5725	Approved
0.6296	Remote Similarity	NPD7427	Discontinued
0.6293	Remote Similarity	NPD5038	Approved
0.6293	Remote Similarity	NPD4434	Approved
0.6293	Remote Similarity	NPD5037	Approved
0.6287	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD826	Approved
0.6278	Remote Similarity	NPD6623	Phase 3
0.6278	Remote Similarity	NPD8416	Discontinued
0.6278	Remote Similarity	NPD825	Approved
0.6277	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3536	Discontinued
0.6276	Remote Similarity	NPD2904	Discontinued
0.6276	Remote Similarity	NPD6746	Phase 2
0.6274	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5772	Approved
0.6269	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5557	Phase 1
0.6269	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5773	Approved
0.6268	Remote Similarity	NPD7669	Phase 3
0.6268	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7820	Phase 3
0.6264	Remote Similarity	NPD3553	Approved
0.6264	Remote Similarity	NPD3552	Approved
0.6264	Remote Similarity	NPD3555	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