NPASS Compound

Structure

NPC228669 OpenBabel07101719252D 32 37 0 0 1 0 0 0 0 0999 V2000 1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0201 -0.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8480 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6567 0.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9820 4.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1160 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5801 2.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9820 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7141 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1160 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7141 4.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7111 -0.0302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8480 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5801 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1160 2.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9820 2.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2500 2.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7111 1.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2989 0.7788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8480 2.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2500 1.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4461 4.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.2788 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 6 7 1 0 0 0 0 6 17 1 0 0 0 0 8 10 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 1 1 6 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 2 1 1 0 0 0 15 26 1 0 0 0 0 16 3 1 6 0 0 0 16 23 1 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 18 29 2 0 0 0 0 19 7 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 27 1 1 0 0 0 21 28 1 1 0 0 0 22 13 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 28 1 1 0 0 0 24 25 1 0 0 0 0 24 32 1 6 0 0 0 25 31 1 6 0 0 0 26 30 2 0 0 0 0 26 32 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.28
Volume:	466.12
LogP:	5.703
LogD:	4.787
LogS:	-5.449
# Rotatable Bonds:	1
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	5.247
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.726
MDCK Permeability:	7.638364331796765e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	84.11170196533203%
Volume Distribution (VD):	1.81
Pgp-substrate:	12.133208274841309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.256
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.73

ADMET: Excretion

Clearance (CL):	19.576
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.729
Human Hepatotoxicity (H-HT):	0.626
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.828
Skin Sensitization:	0.929
Carcinogencity:	0.652
Eye Corrosion:	0.527
Eye Irritation:	0.034
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC228669

Natural Product ID:	NPC228669
*Common Name:**	JCDWJZKYFNMRNW-AHYGXKIUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JCDWJZKYFNMRNW-AHYGXKIUSA-N
Standard InCHI:	InChI=1S/C28H38O4/c1-14-15(2)26(30)32-24(14)25-16(3)23-22(31-25)13-21-19-7-6-17-12-18(29)8-10-27(17,4)20(19)9-11-28(21,23)5/h8,10,12,14-16,19-25H,6-7,9,11,13H2,1-5H3/t14-,15-,16+,19-,20+,21+,22+,23+,24+,25-,27+,28+/m1/s1
SMILES:	C[C@@H]1[C@@H](C)C(=O)O[C@@H]1[C@H]1[C@@H](C)[C@H]2[C@H](C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4CC[C@]23C)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431874
PubChem CID:	72703679
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO25915	Sinularia dura	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18630962]
NPO25915	Sinularia dura	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24128077]
NPO25915	Sinularia dura	Species	Alcyoniidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	4.8	uM	PMID[536586]
NPT112	Cell Line	MOLT-4	Homo sapiens	ED50	=	4.8	uM	PMID[536586]
NPT168	Cell Line	P388	Mus musculus	ED50	=	9.1	uM	PMID[536586]

☑ 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 NPC228669 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	255
0.1-0.2	1462
0.2-0.3	5976
0.3-0.4	13109
0.4-0.5	8079
0.5-0.6	7452
0.6-0.7	5375
0.7-0.8	955
0.8-0.85	27
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC164835
0.9109	High Similarity	NPC96377
0.901	High Similarity	NPC255309
0.8889	High Similarity	NPC271387
0.8889	High Similarity	NPC153792
0.8878	High Similarity	NPC111684
0.8878	High Similarity	NPC58052
0.8785	High Similarity	NPC471398
0.8571	High Similarity	NPC470269
0.8544	High Similarity	NPC140723
0.8542	High Similarity	NPC28227
0.8469	Intermediate Similarity	NPC218301
0.8416	Intermediate Similarity	NPC292133
0.8365	Intermediate Similarity	NPC36321
0.8333	Intermediate Similarity	NPC214797
0.8333	Intermediate Similarity	NPC118860
0.8333	Intermediate Similarity	NPC231589
0.8333	Intermediate Similarity	NPC195640
0.8318	Intermediate Similarity	NPC241927
0.8318	Intermediate Similarity	NPC258543
0.8317	Intermediate Similarity	NPC322063
0.83	Intermediate Similarity	NPC294266
0.8273	Intermediate Similarity	NPC474181
0.8269	Intermediate Similarity	NPC271266
0.8269	Intermediate Similarity	NPC308351
0.8257	Intermediate Similarity	NPC170487
0.8252	Intermediate Similarity	NPC218383
0.8241	Intermediate Similarity	NPC197428
0.8235	Intermediate Similarity	NPC187159
0.8229	Intermediate Similarity	NPC470223
0.8229	Intermediate Similarity	NPC323765
0.8208	Intermediate Similarity	NPC469874
0.8208	Intermediate Similarity	NPC470309
0.8205	Intermediate Similarity	NPC473888
0.8198	Intermediate Similarity	NPC266728
0.8198	Intermediate Similarity	NPC49492
0.8182	Intermediate Similarity	NPC52634
0.8155	Intermediate Similarity	NPC176845
0.8148	Intermediate Similarity	NPC304495
0.8142	Intermediate Similarity	NPC475520
0.8137	Intermediate Similarity	NPC42042
0.8131	Intermediate Similarity	NPC220974
0.8125	Intermediate Similarity	NPC100391
0.8125	Intermediate Similarity	NPC284068
0.8119	Intermediate Similarity	NPC472223
0.8119	Intermediate Similarity	NPC472224
0.8119	Intermediate Similarity	NPC56525
0.8113	Intermediate Similarity	NPC471293
0.8113	Intermediate Similarity	NPC235889
0.8095	Intermediate Similarity	NPC22388
0.8091	Intermediate Similarity	NPC71348
0.8073	Intermediate Similarity	NPC5284
0.807	Intermediate Similarity	NPC474585
0.8058	Intermediate Similarity	NPC475894
0.8053	Intermediate Similarity	NPC473720
0.8039	Intermediate Similarity	NPC469599
0.8037	Intermediate Similarity	NPC470267
0.8037	Intermediate Similarity	NPC181265
0.8037	Intermediate Similarity	NPC196528
0.8037	Intermediate Similarity	NPC291643
0.8036	Intermediate Similarity	NPC270958
0.8036	Intermediate Similarity	NPC190286
0.802	Intermediate Similarity	NPC79117
0.8018	Intermediate Similarity	NPC250109
0.8018	Intermediate Similarity	NPC962
0.8	Intermediate Similarity	NPC310981
0.7982	Intermediate Similarity	NPC473203
0.7981	Intermediate Similarity	NPC114274
0.7981	Intermediate Similarity	NPC471582
0.7963	Intermediate Similarity	NPC59530
0.7961	Intermediate Similarity	NPC471775
0.7946	Intermediate Similarity	NPC326542
0.7946	Intermediate Similarity	NPC123117
0.7944	Intermediate Similarity	NPC29705
0.7944	Intermediate Similarity	NPC189616
0.7928	Intermediate Similarity	NPC207251
0.7925	Intermediate Similarity	NPC473928
0.7921	Intermediate Similarity	NPC154101
0.7917	Intermediate Similarity	NPC100297
0.7913	Intermediate Similarity	NPC109973
0.7909	Intermediate Similarity	NPC239097
0.7905	Intermediate Similarity	NPC167974
0.79	Intermediate Similarity	NPC305039
0.79	Intermediate Similarity	NPC477943
0.7895	Intermediate Similarity	NPC153440
0.7895	Intermediate Similarity	NPC118638
0.789	Intermediate Similarity	NPC61411
0.789	Intermediate Similarity	NPC19412
0.7885	Intermediate Similarity	NPC23680
0.7885	Intermediate Similarity	NPC108078
0.7885	Intermediate Similarity	NPC226986
0.7879	Intermediate Similarity	NPC167877
0.7876	Intermediate Similarity	NPC148458
0.7876	Intermediate Similarity	NPC243981
0.787	Intermediate Similarity	NPC231530
0.787	Intermediate Similarity	NPC475571
0.787	Intermediate Similarity	NPC102352
0.787	Intermediate Similarity	NPC278628
0.7864	Intermediate Similarity	NPC281134
0.7857	Intermediate Similarity	NPC470120
0.7857	Intermediate Similarity	NPC202889
0.785	Intermediate Similarity	NPC254202
0.785	Intermediate Similarity	NPC264048
0.7843	Intermediate Similarity	NPC475657
0.7843	Intermediate Similarity	NPC472225
0.7843	Intermediate Similarity	NPC472226
0.7843	Intermediate Similarity	NPC206810
0.783	Intermediate Similarity	NPC474327
0.783	Intermediate Similarity	NPC476223
0.783	Intermediate Similarity	NPC224720
0.783	Intermediate Similarity	NPC476240
0.7826	Intermediate Similarity	NPC475041
0.7826	Intermediate Similarity	NPC5292
0.7822	Intermediate Similarity	NPC474842
0.7822	Intermediate Similarity	NPC475965
0.7815	Intermediate Similarity	NPC287423
0.781	Intermediate Similarity	NPC477854
0.781	Intermediate Similarity	NPC197386
0.781	Intermediate Similarity	NPC252295
0.7807	Intermediate Similarity	NPC239273
0.7798	Intermediate Similarity	NPC471601
0.7798	Intermediate Similarity	NPC144854
0.7798	Intermediate Similarity	NPC3316
0.7798	Intermediate Similarity	NPC44063
0.7797	Intermediate Similarity	NPC8369
0.7797	Intermediate Similarity	NPC473255
0.7788	Intermediate Similarity	NPC473898
0.7778	Intermediate Similarity	NPC222688
0.7778	Intermediate Similarity	NPC472228
0.7778	Intermediate Similarity	NPC96268
0.7778	Intermediate Similarity	NPC169843
0.7778	Intermediate Similarity	NPC13385
0.7778	Intermediate Similarity	NPC264127
0.7778	Intermediate Similarity	NPC472227
0.7778	Intermediate Similarity	NPC471042
0.7768	Intermediate Similarity	NPC234042
0.7768	Intermediate Similarity	NPC100267
0.7768	Intermediate Similarity	NPC471570
0.7768	Intermediate Similarity	NPC280782
0.7768	Intermediate Similarity	NPC236217
0.7768	Intermediate Similarity	NPC152117
0.7768	Intermediate Similarity	NPC475524
0.7767	Intermediate Similarity	NPC128488
0.7767	Intermediate Similarity	NPC304968
0.7759	Intermediate Similarity	NPC4548
0.7759	Intermediate Similarity	NPC79579
0.7757	Intermediate Similarity	NPC473163
0.7748	Intermediate Similarity	NPC473627
0.7748	Intermediate Similarity	NPC179642
0.7748	Intermediate Similarity	NPC37116
0.7748	Intermediate Similarity	NPC253906
0.7748	Intermediate Similarity	NPC76084
0.7745	Intermediate Similarity	NPC290651
0.7745	Intermediate Similarity	NPC470230
0.7745	Intermediate Similarity	NPC221282
0.7745	Intermediate Similarity	NPC150383
0.7739	Intermediate Similarity	NPC475372
0.7739	Intermediate Similarity	NPC475913
0.7739	Intermediate Similarity	NPC470420
0.7736	Intermediate Similarity	NPC476274
0.7736	Intermediate Similarity	NPC471041
0.7736	Intermediate Similarity	NPC474720
0.7731	Intermediate Similarity	NPC174367
0.7731	Intermediate Similarity	NPC47113
0.7727	Intermediate Similarity	NPC154608
0.7727	Intermediate Similarity	NPC258323
0.7727	Intermediate Similarity	NPC472825
0.7727	Intermediate Similarity	NPC469844
0.7727	Intermediate Similarity	NPC192813
0.7727	Intermediate Similarity	NPC277017
0.7727	Intermediate Similarity	NPC94529
0.7723	Intermediate Similarity	NPC177141
0.7723	Intermediate Similarity	NPC474679
0.7723	Intermediate Similarity	NPC473039
0.7719	Intermediate Similarity	NPC176840
0.7719	Intermediate Similarity	NPC298278
0.7719	Intermediate Similarity	NPC196931
0.7714	Intermediate Similarity	NPC107243
0.7714	Intermediate Similarity	NPC57416
0.7712	Intermediate Similarity	NPC473979
0.7706	Intermediate Similarity	NPC127790
0.7699	Intermediate Similarity	NPC317210
0.7699	Intermediate Similarity	NPC471173
0.7699	Intermediate Similarity	NPC471627
0.7699	Intermediate Similarity	NPC178981
0.7699	Intermediate Similarity	NPC194100
0.7692	Intermediate Similarity	NPC280877
0.7692	Intermediate Similarity	NPC310511
0.7692	Intermediate Similarity	NPC33473
0.7692	Intermediate Similarity	NPC46570
0.7692	Intermediate Similarity	NPC204731
0.7692	Intermediate Similarity	NPC274417
0.7686	Intermediate Similarity	NPC231529
0.7685	Intermediate Similarity	NPC474330
0.7685	Intermediate Similarity	NPC221421
0.7685	Intermediate Similarity	NPC474207
0.7685	Intermediate Similarity	NPC159442
0.7685	Intermediate Similarity	NPC95585
0.7685	Intermediate Similarity	NPC471005
0.7685	Intermediate Similarity	NPC470954

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 NPC228669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	1711
0.2-0.3	4255
0.3-0.4	2034
0.4-0.5	481
0.5-0.6	192
0.6-0.7	139
0.7-0.8	106
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8558	High Similarity	NPD6008	Approved
0.8351	Intermediate Similarity	NPD6903	Approved
0.8333	Intermediate Similarity	NPD7334	Approved
0.8333	Intermediate Similarity	NPD6684	Approved
0.8333	Intermediate Similarity	NPD7521	Approved
0.8333	Intermediate Similarity	NPD6409	Approved
0.8333	Intermediate Similarity	NPD5330	Approved
0.8333	Intermediate Similarity	NPD7146	Approved
0.8218	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD5207	Approved
0.798	Intermediate Similarity	NPD5737	Approved
0.798	Intermediate Similarity	NPD6672	Approved
0.7966	Intermediate Similarity	NPD7078	Approved
0.7949	Intermediate Similarity	NPD7492	Approved
0.7928	Intermediate Similarity	NPD8297	Approved
0.7913	Intermediate Similarity	NPD6054	Approved
0.79	Intermediate Similarity	NPD6904	Approved
0.79	Intermediate Similarity	NPD6080	Approved
0.79	Intermediate Similarity	NPD6673	Approved
0.789	Intermediate Similarity	NPD6881	Approved
0.789	Intermediate Similarity	NPD6899	Approved
0.7881	Intermediate Similarity	NPD6616	Approved
0.7838	Intermediate Similarity	NPD6649	Approved
0.7838	Intermediate Similarity	NPD6650	Approved
0.7807	Intermediate Similarity	NPD6009	Approved
0.7798	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD6370	Approved
0.7767	Intermediate Similarity	NPD6001	Approved
0.7759	Intermediate Similarity	NPD6319	Approved
0.775	Intermediate Similarity	NPD7736	Approved
0.7748	Intermediate Similarity	NPD7102	Approved
0.7748	Intermediate Similarity	NPD7290	Approved
0.7748	Intermediate Similarity	NPD6883	Approved
0.7727	Intermediate Similarity	NPD7320	Approved
0.7727	Intermediate Similarity	NPD6011	Approved
0.7714	Intermediate Similarity	NPD6084	Phase 2
0.7714	Intermediate Similarity	NPD6083	Phase 2
0.7712	Intermediate Similarity	NPD7604	Phase 2
0.7706	Intermediate Similarity	NPD6402	Approved
0.7706	Intermediate Similarity	NPD5739	Approved
0.7706	Intermediate Similarity	NPD7128	Approved
0.7706	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6015	Approved
0.7692	Intermediate Similarity	NPD5983	Phase 2
0.7692	Intermediate Similarity	NPD6016	Approved
0.7679	Intermediate Similarity	NPD6617	Approved
0.7679	Intermediate Similarity	NPD6869	Approved
0.7679	Intermediate Similarity	NPD6847	Approved
0.7679	Intermediate Similarity	NPD8130	Phase 1
0.767	Intermediate Similarity	NPD6399	Phase 3
0.7658	Intermediate Similarity	NPD6012	Approved
0.7658	Intermediate Similarity	NPD6013	Approved
0.7658	Intermediate Similarity	NPD6014	Approved
0.7658	Intermediate Similarity	NPD6373	Approved
0.7658	Intermediate Similarity	NPD6372	Approved
0.7642	Intermediate Similarity	NPD5696	Approved
0.7636	Intermediate Similarity	NPD6412	Phase 2
0.7627	Intermediate Similarity	NPD5988	Approved
0.7624	Intermediate Similarity	NPD5208	Approved
0.7611	Intermediate Similarity	NPD6882	Approved
0.7607	Intermediate Similarity	NPD6059	Approved
0.76	Intermediate Similarity	NPD6098	Approved
0.7583	Intermediate Similarity	NPD6336	Discontinued
0.7573	Intermediate Similarity	NPD6079	Approved
0.7573	Intermediate Similarity	NPD5693	Phase 1
0.7573	Intermediate Similarity	NPD5694	Approved
0.7573	Intermediate Similarity	NPD6050	Approved
0.7524	Intermediate Similarity	NPD5695	Phase 3
0.7523	Intermediate Similarity	NPD6052	Approved
0.7521	Intermediate Similarity	NPD8293	Discontinued
0.7477	Intermediate Similarity	NPD5701	Approved
0.7476	Intermediate Similarity	NPD5692	Phase 3
0.7407	Intermediate Similarity	NPD5286	Approved
0.7407	Intermediate Similarity	NPD4696	Approved
0.7407	Intermediate Similarity	NPD5285	Approved
0.7404	Intermediate Similarity	NPD5284	Approved
0.7404	Intermediate Similarity	NPD5281	Approved
0.74	Intermediate Similarity	NPD3665	Phase 1
0.74	Intermediate Similarity	NPD3133	Approved
0.74	Intermediate Similarity	NPD3666	Approved
0.7395	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4629	Approved
0.7358	Intermediate Similarity	NPD5210	Approved
0.7353	Intermediate Similarity	NPD3573	Approved
0.7339	Intermediate Similarity	NPD5223	Approved
0.7321	Intermediate Similarity	NPD6614	Approved
0.7315	Intermediate Similarity	NPD7638	Approved
0.729	Intermediate Similarity	NPD5222	Approved
0.729	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5221	Approved
0.7288	Intermediate Similarity	NPD6335	Approved
0.7281	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD7900	Approved
0.7264	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7640	Approved
0.7248	Intermediate Similarity	NPD7639	Approved
0.7227	Intermediate Similarity	NPD7101	Approved
0.7227	Intermediate Similarity	NPD7100	Approved
0.7222	Intermediate Similarity	NPD4755	Approved
0.7222	Intermediate Similarity	NPD5173	Approved
0.7212	Intermediate Similarity	NPD4753	Phase 2
0.7207	Intermediate Similarity	NPD5174	Approved
0.7207	Intermediate Similarity	NPD5175	Approved
0.7203	Intermediate Similarity	NPD6317	Approved
0.7203	Intermediate Similarity	NPD7115	Discovery
0.72	Intermediate Similarity	NPD4221	Approved
0.72	Intermediate Similarity	NPD4223	Phase 3
0.7177	Intermediate Similarity	NPD6033	Approved
0.7157	Intermediate Similarity	NPD5329	Approved
0.7157	Intermediate Similarity	NPD1694	Approved
0.7155	Intermediate Similarity	NPD6053	Discontinued
0.7154	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD6313	Approved
0.713	Intermediate Similarity	NPD4697	Phase 3
0.7119	Intermediate Similarity	NPD6274	Approved
0.7119	Intermediate Similarity	NPD6868	Approved
0.7103	Intermediate Similarity	NPD7748	Approved
0.7091	Intermediate Similarity	NPD4700	Approved
0.7087	Intermediate Similarity	NPD5690	Phase 2
0.7087	Intermediate Similarity	NPD3618	Phase 1
0.7064	Intermediate Similarity	NPD7902	Approved
0.7059	Intermediate Similarity	NPD4786	Approved
0.7059	Intermediate Similarity	NPD4197	Approved
0.7048	Intermediate Similarity	NPD6051	Approved
0.7037	Intermediate Similarity	NPD5654	Approved
0.703	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4202	Approved
0.6992	Remote Similarity	NPD6067	Discontinued
0.6984	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD6686	Approved
0.6957	Remote Similarity	NPD4730	Approved
0.6957	Remote Similarity	NPD4729	Approved
0.6929	Remote Similarity	NPD5956	Approved
0.6923	Remote Similarity	NPD4688	Approved
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4689	Approved
0.6923	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4693	Phase 3
0.6923	Remote Similarity	NPD4690	Approved
0.6923	Remote Similarity	NPD5205	Approved
0.6916	Remote Similarity	NPD7515	Phase 2
0.6909	Remote Similarity	NPD5959	Approved
0.6903	Remote Similarity	NPD4754	Approved
0.69	Remote Similarity	NPD4195	Approved
0.6893	Remote Similarity	NPD3668	Phase 3
0.6863	Remote Similarity	NPD3667	Approved
0.6838	Remote Similarity	NPD5249	Phase 3
0.6838	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5251	Approved
0.6838	Remote Similarity	NPD5169	Approved
0.6838	Remote Similarity	NPD5247	Approved
0.6838	Remote Similarity	NPD5135	Approved
0.6838	Remote Similarity	NPD5250	Approved
0.6838	Remote Similarity	NPD5248	Approved
0.6829	Remote Similarity	NPD6909	Approved
0.6829	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD5128	Approved
0.6807	Remote Similarity	NPD6858	Approved
0.6807	Remote Similarity	NPD7094	Approved
0.6796	Remote Similarity	NPD4788	Approved
0.6783	Remote Similarity	NPD4768	Approved
0.6783	Remote Similarity	NPD4767	Approved
0.678	Remote Similarity	NPD5215	Approved
0.678	Remote Similarity	NPD5216	Approved
0.678	Remote Similarity	NPD5217	Approved
0.678	Remote Similarity	NPD5127	Approved
0.6771	Remote Similarity	NPD4747	Approved
0.6771	Remote Similarity	NPD4691	Approved
0.6762	Remote Similarity	NPD5280	Approved
0.6762	Remote Similarity	NPD5279	Phase 3
0.6762	Remote Similarity	NPD4694	Approved
0.6759	Remote Similarity	NPD8035	Phase 2
0.6759	Remote Similarity	NPD8034	Phase 2
0.6744	Remote Similarity	NPD7260	Phase 2
0.6735	Remote Similarity	NPD4058	Approved
0.6724	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8328	Phase 3
0.6701	Remote Similarity	NPD5777	Approved
0.6699	Remote Similarity	NPD6435	Approved
0.6694	Remote Similarity	NPD7503	Approved
0.6692	Remote Similarity	NPD6334	Approved
0.6692	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD7732	Phase 3
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5091	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6641	Remote Similarity	NPD8336	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