NPASS Compound

Structure

NPC474018 OpenBabel07101718232D 37 39 0 0 1 0 0 0 0 0999 V2000 1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7978 8.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1797 6.3427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2308 3.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1293 5.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4894 7.0858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5398 4.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1804 8.0369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8495 8.7800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5405 9.7311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8277 8.5721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 8 37 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 24 1 0 0 0 0 19 26 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 29 1 6 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 25 30 1 0 0 0 0 25 31 1 6 0 0 0 26 31 1 1 0 0 0 26 32 1 0 0 0 0 27 32 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 31 6 1 6 0 0 0 32 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.32
Volume:	559.218
LogP:	5.175
LogD:	4.44
LogS:	-5.069
# Rotatable Bonds:	7
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	4.791
Fsp3:	0.594
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:	-5.08
MDCK Permeability:	2.3267322831088677e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.144
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	92.98129272460938%
Volume Distribution (VD):	0.333
Pgp-substrate:	8.426107406616211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.793
CYP2C19-inhibitor:	0.397
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.665
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.694
CYP2D6-substrate:	0.785
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.43

ADMET: Excretion

Clearance (CL):	1.75
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.166
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.588
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.872
Carcinogencity:	0.855
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC474018

Natural Product ID:	NPC474018
*Common Name:**	Stellettin H
IUPAC Name:	(2E,4E,6E,8E,10E)-10-[(3aS,5aS,7S,9aS,9bS)-7-methoxycarbonyl-3a,6,6,9a-tetramethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid
Synonyms:	stellettin H
Standard InCHIKey:	AZCFRDBOFGFKPT-CDUNGHGCSA-N
Standard InCHI:	InChI=1S/C32H44O5/c1-20(12-10-14-22(3)28(34)35)11-9-13-21(2)27-24(33)19-26-31(6)17-15-23(29(36)37-8)30(4,5)25(31)16-18-32(26,27)7/h9-14,23,25-26H,15-19H2,1-8H3,(H,34,35)/b12-10+,13-9+,20-11+,22-14+,27-21-/t23-,25+,26+,31+,32+/m1/s1
SMILES:	COC(=O)[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@]1([C@H]2CC(=O)/C/1=C(/C=C/C=C(/C=C/C=C(/C(=O)O)C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458460
PubChem CID:	44584140
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	4920.0	nM	PMID[525337]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	3980.0	nM	PMID[525337]

☑ 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 NPC474018 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	158
0.1-0.2	832
0.2-0.3	3604
0.3-0.4	10490
0.4-0.5	12192
0.5-0.6	7821
0.6-0.7	5578
0.7-0.8	1810
0.8-0.85	151
0.85-0.9	52
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473986
0.9121	High Similarity	NPC301534
0.9121	High Similarity	NPC250757
0.9091	High Similarity	NPC66344
0.9059	High Similarity	NPC279639
0.9059	High Similarity	NPC3856
0.9032	High Similarity	NPC266955
0.8977	High Similarity	NPC472870
0.8947	High Similarity	NPC72151
0.8941	High Similarity	NPC469804
0.8941	High Similarity	NPC469805
0.8941	High Similarity	NPC469806
0.8941	High Similarity	NPC469799
0.8936	High Similarity	NPC115899
0.8925	High Similarity	NPC57079
0.8925	High Similarity	NPC108368
0.8889	High Similarity	NPC204341
0.8889	High Similarity	NPC470113
0.8876	High Similarity	NPC262043
0.8864	High Similarity	NPC128644
0.8864	High Similarity	NPC236618
0.8842	High Similarity	NPC320447
0.8837	High Similarity	NPC97913
0.8804	High Similarity	NPC293052
0.8764	High Similarity	NPC117122
0.875	High Similarity	NPC472869
0.875	High Similarity	NPC186975
0.8737	High Similarity	NPC282524
0.8737	High Similarity	NPC99411
0.8736	High Similarity	NPC19849
0.8736	High Similarity	NPC472864
0.8736	High Similarity	NPC164577
0.8706	High Similarity	NPC469798
0.8706	High Similarity	NPC469797
0.8696	High Similarity	NPC299100
0.8667	High Similarity	NPC118011
0.8667	High Similarity	NPC36668
0.8652	High Similarity	NPC136948
0.8646	High Similarity	NPC114540
0.8646	High Similarity	NPC32577
0.8646	High Similarity	NPC155332
0.8636	High Similarity	NPC29447
0.8636	High Similarity	NPC269638
0.8621	High Similarity	NPC474790
0.8621	High Similarity	NPC474976
0.8602	High Similarity	NPC476174
0.8602	High Similarity	NPC180950
0.8602	High Similarity	NPC171395
0.8587	High Similarity	NPC472871
0.8571	High Similarity	NPC475965
0.8571	High Similarity	NPC474842
0.8571	High Similarity	NPC472866
0.8557	High Similarity	NPC475526
0.8557	High Similarity	NPC329345
0.8557	High Similarity	NPC473283
0.8526	High Similarity	NPC235464
0.8526	High Similarity	NPC166745
0.8523	High Similarity	NPC248758
0.8523	High Similarity	NPC472865
0.8511	High Similarity	NPC29152
0.8511	High Similarity	NPC471153
0.8495	Intermediate Similarity	NPC474690
0.8485	Intermediate Similarity	NPC473284
0.8478	Intermediate Similarity	NPC476187
0.8471	Intermediate Similarity	NPC198240
0.8444	Intermediate Similarity	NPC476293
0.8438	Intermediate Similarity	NPC35751
0.8421	Intermediate Similarity	NPC253826
0.8421	Intermediate Similarity	NPC110937
0.8421	Intermediate Similarity	NPC156546
0.8404	Intermediate Similarity	NPC88310
0.8404	Intermediate Similarity	NPC209355
0.8391	Intermediate Similarity	NPC278459
0.8391	Intermediate Similarity	NPC40228
0.8391	Intermediate Similarity	NPC477372
0.8384	Intermediate Similarity	NPC266570
0.8384	Intermediate Similarity	NPC189863
0.837	Intermediate Similarity	NPC477149
0.837	Intermediate Similarity	NPC477147
0.8367	Intermediate Similarity	NPC475050
0.8353	Intermediate Similarity	NPC61952
0.8352	Intermediate Similarity	NPC72397
0.8351	Intermediate Similarity	NPC224720
0.8351	Intermediate Similarity	NPC118174
0.8351	Intermediate Similarity	NPC476240
0.8351	Intermediate Similarity	NPC168319
0.8351	Intermediate Similarity	NPC194028
0.8351	Intermediate Similarity	NPC476223
0.8333	Intermediate Similarity	NPC98868
0.8316	Intermediate Similarity	NPC472941
0.8316	Intermediate Similarity	NPC456
0.8315	Intermediate Similarity	NPC87552
0.8298	Intermediate Similarity	NPC473431
0.8298	Intermediate Similarity	NPC471078
0.8298	Intermediate Similarity	NPC473435
0.8298	Intermediate Similarity	NPC473280
0.8295	Intermediate Similarity	NPC296367
0.8295	Intermediate Similarity	NPC100297
0.8295	Intermediate Similarity	NPC472239
0.8295	Intermediate Similarity	NPC320514
0.8283	Intermediate Similarity	NPC472868
0.8261	Intermediate Similarity	NPC5509
0.8261	Intermediate Similarity	NPC174342
0.8261	Intermediate Similarity	NPC474570
0.8261	Intermediate Similarity	NPC214387
0.8247	Intermediate Similarity	NPC476274
0.8242	Intermediate Similarity	NPC141292
0.8242	Intermediate Similarity	NPC181327
0.8242	Intermediate Similarity	NPC476409
0.8242	Intermediate Similarity	NPC477228
0.8229	Intermediate Similarity	NPC2049
0.8229	Intermediate Similarity	NPC474785
0.8229	Intermediate Similarity	NPC474938
0.8229	Intermediate Similarity	NPC208094
0.8229	Intermediate Similarity	NPC107243
0.8229	Intermediate Similarity	NPC202705
0.8222	Intermediate Similarity	NPC283733
0.8222	Intermediate Similarity	NPC65661
0.8222	Intermediate Similarity	NPC60350
0.8218	Intermediate Similarity	NPC318363
0.8218	Intermediate Similarity	NPC473482
0.8218	Intermediate Similarity	NPC475418
0.8218	Intermediate Similarity	NPC220155
0.8211	Intermediate Similarity	NPC139459
0.8211	Intermediate Similarity	NPC295347
0.8202	Intermediate Similarity	NPC69279
0.8202	Intermediate Similarity	NPC49019
0.8202	Intermediate Similarity	NPC83569
0.8202	Intermediate Similarity	NPC310470
0.8191	Intermediate Similarity	NPC38232
0.8191	Intermediate Similarity	NPC476416
0.8191	Intermediate Similarity	NPC474736
0.8182	Intermediate Similarity	NPC147066
0.8182	Intermediate Similarity	NPC90055
0.8172	Intermediate Similarity	NPC476437
0.8172	Intermediate Similarity	NPC51486
0.8172	Intermediate Similarity	NPC476369
0.8163	Intermediate Similarity	NPC146822
0.8161	Intermediate Similarity	NPC477371
0.8155	Intermediate Similarity	NPC474315
0.8152	Intermediate Similarity	NPC310752
0.8152	Intermediate Similarity	NPC292491
0.8152	Intermediate Similarity	NPC104560
0.8152	Intermediate Similarity	NPC48107
0.8144	Intermediate Similarity	NPC471717
0.8144	Intermediate Similarity	NPC103051
0.8144	Intermediate Similarity	NPC197386
0.814	Intermediate Similarity	NPC97377
0.8137	Intermediate Similarity	NPC475065
0.8132	Intermediate Similarity	NPC322159
0.8132	Intermediate Similarity	NPC6247
0.8125	Intermediate Similarity	NPC151725
0.8125	Intermediate Similarity	NPC106425
0.8125	Intermediate Similarity	NPC122324
0.8125	Intermediate Similarity	NPC328371
0.8119	Intermediate Similarity	NPC330011
0.8119	Intermediate Similarity	NPC475294
0.8119	Intermediate Similarity	NPC329048
0.8118	Intermediate Similarity	NPC469803
0.8118	Intermediate Similarity	NPC476844
0.8111	Intermediate Similarity	NPC16287
0.8111	Intermediate Similarity	NPC181743
0.8111	Intermediate Similarity	NPC165064
0.8111	Intermediate Similarity	NPC194937
0.8111	Intermediate Similarity	NPC476038
0.8111	Intermediate Similarity	NPC178025
0.8105	Intermediate Similarity	NPC8993
0.8105	Intermediate Similarity	NPC124207
0.8105	Intermediate Similarity	NPC469406
0.809	Intermediate Similarity	NPC133391
0.809	Intermediate Similarity	NPC142253
0.809	Intermediate Similarity	NPC240302
0.809	Intermediate Similarity	NPC3511
0.809	Intermediate Similarity	NPC472867
0.8085	Intermediate Similarity	NPC473998
0.8085	Intermediate Similarity	NPC475806
0.8081	Intermediate Similarity	NPC473163
0.8065	Intermediate Similarity	NPC284561
0.8065	Intermediate Similarity	NPC473999
0.8065	Intermediate Similarity	NPC310236
0.8065	Intermediate Similarity	NPC474844
0.8065	Intermediate Similarity	NPC309603
0.8061	Intermediate Similarity	NPC241221
0.8061	Intermediate Similarity	NPC477720
0.8061	Intermediate Similarity	NPC287833
0.8061	Intermediate Similarity	NPC471041
0.8058	Intermediate Similarity	NPC16270
0.8046	Intermediate Similarity	NPC239098
0.8046	Intermediate Similarity	NPC179028
0.8046	Intermediate Similarity	NPC275494
0.8046	Intermediate Similarity	NPC471409
0.8046	Intermediate Similarity	NPC74410
0.8046	Intermediate Similarity	NPC321514
0.8046	Intermediate Similarity	NPC169095
0.8043	Intermediate Similarity	NPC96496
0.8043	Intermediate Similarity	NPC287079
0.8043	Intermediate Similarity	NPC75315
0.8043	Intermediate Similarity	NPC93778
0.8043	Intermediate Similarity	NPC163016
0.8041	Intermediate Similarity	NPC108078

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 NPC474018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1010
0.2-0.3	3382
0.3-0.4	3006
0.4-0.5	1005
0.5-0.6	282
0.6-0.7	189
0.7-0.8	134
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8085	Intermediate Similarity	NPD5281	Approved
0.8085	Intermediate Similarity	NPD5284	Approved
0.7957	Intermediate Similarity	NPD6672	Approved
0.7957	Intermediate Similarity	NPD5737	Approved
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7889	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD6084	Phase 2
0.7812	Intermediate Similarity	NPD6399	Phase 3
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD4519	Discontinued
0.7742	Intermediate Similarity	NPD4623	Approved
0.7732	Intermediate Similarity	NPD7748	Approved
0.7717	Intermediate Similarity	NPD3666	Approved
0.7717	Intermediate Similarity	NPD3133	Approved
0.7717	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD5694	Approved
0.7708	Intermediate Similarity	NPD6079	Approved
0.7708	Intermediate Similarity	NPD6050	Approved
0.77	Intermediate Similarity	NPD6404	Discontinued
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD4223	Phase 3
0.7692	Intermediate Similarity	NPD4221	Approved
0.7684	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6904	Approved
0.7684	Intermediate Similarity	NPD6080	Approved
0.7684	Intermediate Similarity	NPD6673	Approved
0.7653	Intermediate Similarity	NPD5695	Phase 3
0.764	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5329	Approved
0.7604	Intermediate Similarity	NPD5692	Phase 3
0.7604	Intermediate Similarity	NPD5207	Approved
0.7604	Intermediate Similarity	NPD5785	Approved
0.76	Intermediate Similarity	NPD5696	Approved
0.76	Intermediate Similarity	NPD7638	Approved
0.7586	Intermediate Similarity	NPD4058	Approved
0.7553	Intermediate Similarity	NPD5690	Phase 2
0.7553	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5280	Approved
0.7553	Intermediate Similarity	NPD3618	Phase 1
0.7553	Intermediate Similarity	NPD5279	Phase 3
0.7553	Intermediate Similarity	NPD4694	Approved
0.7527	Intermediate Similarity	NPD4197	Approved
0.7527	Intermediate Similarity	NPD4786	Approved
0.7526	Intermediate Similarity	NPD7637	Suspended
0.7526	Intermediate Similarity	NPD5693	Phase 1
0.7526	Intermediate Similarity	NPD7515	Phase 2
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7477	Intermediate Similarity	NPD8130	Phase 1
0.7475	Intermediate Similarity	NPD4629	Approved
0.7475	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5210	Approved
0.7473	Intermediate Similarity	NPD4695	Discontinued
0.7455	Intermediate Similarity	NPD7115	Discovery
0.7447	Intermediate Similarity	NPD5363	Approved
0.7444	Intermediate Similarity	NPD3617	Approved
0.7429	Intermediate Similarity	NPD5697	Approved
0.7407	Intermediate Similarity	NPD8297	Approved
0.74	Intermediate Similarity	NPD5221	Approved
0.74	Intermediate Similarity	NPD5222	Approved
0.74	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5208	Approved
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7379	Intermediate Similarity	NPD5211	Phase 2
0.7368	Intermediate Similarity	NPD4693	Phase 3
0.7368	Intermediate Similarity	NPD4690	Approved
0.7368	Intermediate Similarity	NPD5205	Approved
0.7368	Intermediate Similarity	NPD4689	Approved
0.7368	Intermediate Similarity	NPD4138	Approved
0.7368	Intermediate Similarity	NPD4688	Approved
0.7368	Intermediate Similarity	NPD6098	Approved
0.7363	Intermediate Similarity	NPD4195	Approved
0.7358	Intermediate Similarity	NPD6011	Approved
0.7333	Intermediate Similarity	NPD7128	Approved
0.7333	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD6675	Approved
0.7333	Intermediate Similarity	NPD6402	Approved
0.7327	Intermediate Similarity	NPD5173	Approved
0.7315	Intermediate Similarity	NPD6649	Approved
0.7315	Intermediate Similarity	NPD6869	Approved
0.7315	Intermediate Similarity	NPD6650	Approved
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.729	Intermediate Similarity	NPD6014	Approved
0.729	Intermediate Similarity	NPD6013	Approved
0.729	Intermediate Similarity	NPD6012	Approved
0.7263	Intermediate Similarity	NPD1694	Approved
0.7248	Intermediate Similarity	NPD6882	Approved
0.7241	Intermediate Similarity	NPD4691	Approved
0.7238	Intermediate Similarity	NPD5141	Approved
0.7234	Intermediate Similarity	NPD5362	Discontinued
0.7234	Intermediate Similarity	NPD4788	Approved
0.72	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7900	Approved
0.7196	Intermediate Similarity	NPD7320	Approved
0.7191	Intermediate Similarity	NPD4687	Approved
0.7191	Intermediate Similarity	NPD5733	Approved
0.7184	Intermediate Similarity	NPD5286	Approved
0.7184	Intermediate Similarity	NPD5285	Approved
0.7184	Intermediate Similarity	NPD4696	Approved
0.7172	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD8034	Phase 2
0.7158	Intermediate Similarity	NPD3668	Phase 3
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.7129	Intermediate Similarity	NPD5654	Approved
0.7128	Intermediate Similarity	NPD4269	Approved
0.7128	Intermediate Similarity	NPD4270	Approved
0.7126	Intermediate Similarity	NPD4137	Phase 3
0.7115	Intermediate Similarity	NPD5223	Approved
0.7111	Intermediate Similarity	NPD8039	Approved
0.7103	Intermediate Similarity	NPD5701	Approved
0.71	Intermediate Similarity	NPD5779	Approved
0.71	Intermediate Similarity	NPD5778	Approved
0.71	Intermediate Similarity	NPD4202	Approved
0.7087	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4096	Approved
0.7059	Intermediate Similarity	NPD7732	Phase 3
0.7059	Intermediate Similarity	NPD7614	Phase 1
0.7059	Intermediate Similarity	NPD4697	Phase 3
0.7054	Intermediate Similarity	NPD6868	Approved
0.7048	Intermediate Similarity	NPD4633	Approved
0.7048	Intermediate Similarity	NPD5226	Approved
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.7048	Intermediate Similarity	NPD5224	Approved
0.7048	Intermediate Similarity	NPD5225	Approved
0.7045	Intermediate Similarity	NPD4747	Approved
0.7041	Intermediate Similarity	NPD4518	Approved
0.7037	Intermediate Similarity	NPD6686	Approved
0.703	Intermediate Similarity	NPD6001	Approved
0.7027	Intermediate Similarity	NPD4632	Approved
0.701	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6411	Approved
0.699	Remote Similarity	NPD5959	Approved
0.699	Remote Similarity	NPD4755	Approved
0.6981	Remote Similarity	NPD5175	Approved
0.6981	Remote Similarity	NPD5174	Approved
0.6966	Remote Similarity	NPD5276	Approved
0.6957	Remote Similarity	NPD4756	Discovery
0.6944	Remote Similarity	NPD6412	Phase 2
0.6944	Remote Similarity	NPD6614	Approved
0.6931	Remote Similarity	NPD5133	Approved
0.693	Remote Similarity	NPD6335	Approved
0.6915	Remote Similarity	NPD4252	Approved
0.6887	Remote Similarity	NPD5091	Approved
0.6875	Remote Similarity	NPD7154	Phase 3
0.6875	Remote Similarity	NPD6695	Phase 3
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7100	Approved
0.6857	Remote Similarity	NPD4700	Approved
0.6842	Remote Similarity	NPD6317	Approved
0.6842	Remote Similarity	NPD5369	Approved
0.6842	Remote Similarity	NPD6009	Approved
0.6822	Remote Similarity	NPD6052	Approved
0.6813	Remote Similarity	NPD6926	Approved
0.6813	Remote Similarity	NPD6924	Approved
0.6809	Remote Similarity	NPD6929	Approved
0.6804	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6051	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6101	Approved
0.6783	Remote Similarity	NPD6314	Approved
0.6783	Remote Similarity	NPD6313	Approved
0.6778	Remote Similarity	NPD6081	Approved
0.6771	Remote Similarity	NPD5209	Approved
0.6771	Remote Similarity	NPD6435	Approved
0.6768	Remote Similarity	NPD7750	Discontinued
0.6754	Remote Similarity	NPD6274	Approved
0.6737	Remote Similarity	NPD4819	Approved
0.6737	Remote Similarity	NPD5368	Approved
0.6737	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6930	Phase 2
0.6737	Remote Similarity	NPD4821	Approved
0.6737	Remote Similarity	NPD4820	Approved
0.6737	Remote Similarity	NPD7514	Phase 3
0.6737	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4822	Approved
0.6737	Remote Similarity	NPD6931	Approved
0.6735	Remote Similarity	NPD1696	Phase 3
0.6727	Remote Similarity	NPD4730	Approved
0.6727	Remote Similarity	NPD5168	Approved
0.6727	Remote Similarity	NPD4729	Approved
0.6726	Remote Similarity	NPD7094	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