NPASS Compound

Structure

NPC17336 OpenBabel07101718312D 35 39 0 0 1 0 0 0 0 0999 V2000 -4.7684 7.7041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0639 6.1218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4997 5.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5955 6.8906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3936 4.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7000 5.8961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 2.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -1.7245 3.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4154 4.6535 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 -5.9956 4.3138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8730 6.7096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0875 4.6160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7865 6.3028 0.0000 C 0 0 2 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 -3.6808 3.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0820 4.7205 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 -2.7026 3.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8910 5.3083 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0846 5.3966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 31 1 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 17 3 1 1 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 4 1 6 0 0 0 18 28 1 0 0 0 0 19 32 1 6 0 0 0 20 27 1 6 0 0 0 21 23 1 0 0 0 0 21 27 1 6 0 0 0 22 28 1 1 0 0 0 23 24 1 0 0 0 0 23 25 1 1 0 0 0 24 26 1 0 0 0 0 24 33 1 6 0 0 0 25 29 1 0 0 0 0 25 34 2 0 0 0 0 26 30 1 1 0 0 0 26 35 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 14 1 6 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	525.968
LogP:	4.352
LogD:	5.118
LogS:	-4.262
# Rotatable Bonds:	7
TPSA:	90.29
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	6.045
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
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:	-4.77
MDCK Permeability:	2.4245608074124902e-05
Pgp-inhibitor:	0.899
Pgp-substrate:	0.222
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.282
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	94.37633514404297%
Volume Distribution (VD):	0.973
Pgp-substrate:	1.7311698198318481%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.714
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.794

ADMET: Excretion

Clearance (CL):	8.86
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.35
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.597
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.17
Carcinogencity:	0.034
Eye Corrosion:	0.553
Eye Irritation:	0.105
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC17336

Natural Product ID:	NPC17336
*Common Name:**	3Beta,7Beta-11-Trihydroxy-5Alpha,6Alpha-Epoxy-9,11-Secogorgostan-9-One
IUPAC Name:	(1aS,2R,3R,4aS,7S,8aR)-2,7-dihydroxy-3-[(1S,2R,3R)-2-(2-hydroxyethyl)-2-methyl-3-[(1S)-1-[(1R,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]cyclopentyl]-4a-methyl-2,3,5,6,7,8-hexahydro-1aH-naphtho[4,4a-b]oxiren-4-one
Synonyms:
Standard InCHIKey:	HLIKJFSNOAKWBO-YTVAPMNTSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-16(2)18(4)28(6)15-22(28)17(3)20-8-9-21(27(20,5)12-13-31)23-24(33)26-30(35-26)14-19(32)10-11-29(30,7)25(23)34/h16-24,26,31-33H,8-15H2,1-7H3/t17-,18+,19-,20+,21-,22+,23+,24+,26-,27+,28+,29+,30-/m0/s1
SMILES:	CC(C)[C@@H](C)[C@@]1(C)C[C@@H]1[C@@H](C)[C@H]1CC[C@@H]([C@@H]2[C@H]([C@H]3[C@]4(C[C@H](CC[C@]4(C)C2=O)O)O3)O)[C@]1(C)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473661
PubChem CID:	10719879
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO11349	Lobophytum sp.	Species	Alcyoniidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[9584407]
NPO11349	Lobophytum sp.	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	6300.0	nM	PMID[531293]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	7100.0	nM	PMID[531293]

☑ 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 NPC17336 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	467
0.1-0.2	3608
0.2-0.3	8406
0.3-0.4	14067
0.4-0.5	6679
0.5-0.6	6292
0.6-0.7	2740
0.7-0.8	415
0.8-0.85	15
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC477614
0.9318	High Similarity	NPC226491
0.8876	High Similarity	NPC474215
0.8876	High Similarity	NPC475729
0.8778	High Similarity	NPC263802
0.8778	High Similarity	NPC202937
0.8587	High Similarity	NPC61688
0.8542	High Similarity	NPC190080
0.8542	High Similarity	NPC111187
0.8539	High Similarity	NPC227170
0.8444	Intermediate Similarity	NPC50438
0.8438	Intermediate Similarity	NPC477264
0.8387	Intermediate Similarity	NPC24705
0.8387	Intermediate Similarity	NPC56962
0.8384	Intermediate Similarity	NPC471254
0.8352	Intermediate Similarity	NPC473350
0.83	Intermediate Similarity	NPC34562
0.8261	Intermediate Similarity	NPC80700
0.8261	Intermediate Similarity	NPC472745
0.8247	Intermediate Similarity	NPC116683
0.8242	Intermediate Similarity	NPC475689
0.8229	Intermediate Similarity	NPC477495
0.82	Intermediate Similarity	NPC470172
0.8172	Intermediate Similarity	NPC239938
0.8144	Intermediate Similarity	NPC62407
0.8144	Intermediate Similarity	NPC287354
0.8125	Intermediate Similarity	NPC476189
0.8119	Intermediate Similarity	NPC471253
0.8119	Intermediate Similarity	NPC473406
0.8085	Intermediate Similarity	NPC476435
0.8085	Intermediate Similarity	NPC476379
0.8081	Intermediate Similarity	NPC253995
0.8081	Intermediate Similarity	NPC476294
0.8065	Intermediate Similarity	NPC302111
0.8061	Intermediate Similarity	NPC163685
0.8061	Intermediate Similarity	NPC235109
0.8043	Intermediate Similarity	NPC477434
0.8041	Intermediate Similarity	NPC470423
0.8041	Intermediate Similarity	NPC470424
0.8039	Intermediate Similarity	NPC470167
0.8	Intermediate Similarity	NPC16449
0.798	Intermediate Similarity	NPC170978
0.7978	Intermediate Similarity	NPC475725
0.7959	Intermediate Similarity	NPC82633
0.7959	Intermediate Similarity	NPC470031
0.7944	Intermediate Similarity	NPC97002
0.7941	Intermediate Similarity	NPC107385
0.7935	Intermediate Similarity	NPC268578
0.7935	Intermediate Similarity	NPC472744
0.7935	Intermediate Similarity	NPC292458
0.7935	Intermediate Similarity	NPC217559
0.7925	Intermediate Similarity	NPC473062
0.7921	Intermediate Similarity	NPC298266
0.7921	Intermediate Similarity	NPC178853
0.7921	Intermediate Similarity	NPC259654
0.7895	Intermediate Similarity	NPC471221
0.7885	Intermediate Similarity	NPC166993
0.7872	Intermediate Similarity	NPC476727
0.7872	Intermediate Similarity	NPC476726
0.7872	Intermediate Similarity	NPC474448
0.787	Intermediate Similarity	NPC470116
0.787	Intermediate Similarity	NPC470115
0.785	Intermediate Similarity	NPC477492
0.785	Intermediate Similarity	NPC477489
0.7849	Intermediate Similarity	NPC473336
0.7849	Intermediate Similarity	NPC471044
0.7835	Intermediate Similarity	NPC52756
0.7835	Intermediate Similarity	NPC216137
0.7826	Intermediate Similarity	NPC317066
0.7812	Intermediate Similarity	NPC477440
0.7812	Intermediate Similarity	NPC477443
0.7812	Intermediate Similarity	NPC200580
0.781	Intermediate Similarity	NPC273155
0.78	Intermediate Similarity	NPC471241
0.7789	Intermediate Similarity	NPC5943
0.7788	Intermediate Similarity	NPC470587
0.7788	Intermediate Similarity	NPC138908
0.7788	Intermediate Similarity	NPC200957
0.7778	Intermediate Similarity	NPC471769
0.7767	Intermediate Similarity	NPC209298
0.7767	Intermediate Similarity	NPC277074
0.7736	Intermediate Similarity	NPC227879
0.7736	Intermediate Similarity	NPC208333
0.7732	Intermediate Similarity	NPC77756
0.7732	Intermediate Similarity	NPC477442
0.7732	Intermediate Similarity	NPC477433
0.7732	Intermediate Similarity	NPC476296
0.7732	Intermediate Similarity	NPC477444
0.7717	Intermediate Similarity	NPC254123
0.7717	Intermediate Similarity	NPC469745
0.77	Intermediate Similarity	NPC193785
0.77	Intermediate Similarity	NPC476728
0.7692	Intermediate Similarity	NPC100078
0.7692	Intermediate Similarity	NPC275243
0.7692	Intermediate Similarity	NPC301787
0.7684	Intermediate Similarity	NPC476717
0.7684	Intermediate Similarity	NPC131365
0.7684	Intermediate Similarity	NPC472272
0.7684	Intermediate Similarity	NPC83242
0.7679	Intermediate Similarity	NPC251226
0.7679	Intermediate Similarity	NPC154491
0.7679	Intermediate Similarity	NPC268530
0.7677	Intermediate Similarity	NPC76136
0.7677	Intermediate Similarity	NPC217567
0.7677	Intermediate Similarity	NPC329713
0.7667	Intermediate Similarity	NPC475031
0.7667	Intermediate Similarity	NPC264602
0.766	Intermediate Similarity	NPC319909
0.7647	Intermediate Similarity	NPC94906
0.7647	Intermediate Similarity	NPC41843
0.7642	Intermediate Similarity	NPC218123
0.7642	Intermediate Similarity	NPC112895
0.7642	Intermediate Similarity	NPC231278
0.764	Intermediate Similarity	NPC472952
0.764	Intermediate Similarity	NPC472950
0.7634	Intermediate Similarity	NPC202688
0.7634	Intermediate Similarity	NPC154043
0.7634	Intermediate Similarity	NPC121121
0.7634	Intermediate Similarity	NPC60018
0.7629	Intermediate Similarity	NPC67653
0.7629	Intermediate Similarity	NPC471459
0.7624	Intermediate Similarity	NPC472273
0.7619	Intermediate Similarity	NPC166079
0.7619	Intermediate Similarity	NPC307660
0.7619	Intermediate Similarity	NPC130511
0.7619	Intermediate Similarity	NPC222833
0.7615	Intermediate Similarity	NPC317210
0.7611	Intermediate Similarity	NPC159456
0.7611	Intermediate Similarity	NPC4021
0.7609	Intermediate Similarity	NPC472943
0.7609	Intermediate Similarity	NPC470609
0.7609	Intermediate Similarity	NPC472951
0.7596	Intermediate Similarity	NPC122811
0.7593	Intermediate Similarity	NPC474229
0.7582	Intermediate Similarity	NPC147993
0.7579	Intermediate Similarity	NPC477445
0.7579	Intermediate Similarity	NPC266651
0.7579	Intermediate Similarity	NPC477205
0.7576	Intermediate Similarity	NPC474379
0.7573	Intermediate Similarity	NPC46848
0.7565	Intermediate Similarity	NPC469790
0.7556	Intermediate Similarity	NPC472487
0.7556	Intermediate Similarity	NPC472486
0.7553	Intermediate Similarity	NPC15091
0.7553	Intermediate Similarity	NPC269684
0.7553	Intermediate Similarity	NPC327451
0.7551	Intermediate Similarity	NPC475056
0.7551	Intermediate Similarity	NPC470114
0.7551	Intermediate Similarity	NPC185529
0.7551	Intermediate Similarity	NPC472146
0.7549	Intermediate Similarity	NPC472144
0.7549	Intermediate Similarity	NPC472028
0.7547	Intermediate Similarity	NPC473165
0.7527	Intermediate Similarity	NPC12933
0.7526	Intermediate Similarity	NPC90676
0.7525	Intermediate Similarity	NPC475785
0.7524	Intermediate Similarity	NPC88469
0.7523	Intermediate Similarity	NPC476964
0.75	Intermediate Similarity	NPC275990
0.75	Intermediate Similarity	NPC474786
0.75	Intermediate Similarity	NPC245029
0.75	Intermediate Similarity	NPC81074
0.75	Intermediate Similarity	NPC477282
0.75	Intermediate Similarity	NPC137104
0.75	Intermediate Similarity	NPC215968
0.75	Intermediate Similarity	NPC269333
0.75	Intermediate Similarity	NPC235196
0.75	Intermediate Similarity	NPC85391
0.75	Intermediate Similarity	NPC228593
0.75	Intermediate Similarity	NPC244969
0.75	Intermediate Similarity	NPC31302
0.75	Intermediate Similarity	NPC309127
0.75	Intermediate Similarity	NPC247877
0.75	Intermediate Similarity	NPC320383
0.75	Intermediate Similarity	NPC213528
0.75	Intermediate Similarity	NPC155531
0.75	Intermediate Similarity	NPC124544
0.7477	Intermediate Similarity	NPC89860
0.7477	Intermediate Similarity	NPC189663
0.7477	Intermediate Similarity	NPC475490
0.7477	Intermediate Similarity	NPC473410
0.7477	Intermediate Similarity	NPC289702
0.7477	Intermediate Similarity	NPC471094
0.7477	Intermediate Similarity	NPC469984
0.7477	Intermediate Similarity	NPC208461
0.7477	Intermediate Similarity	NPC63841
0.7477	Intermediate Similarity	NPC55973
0.7477	Intermediate Similarity	NPC469826
0.7476	Intermediate Similarity	NPC37047
0.7476	Intermediate Similarity	NPC470388
0.7476	Intermediate Similarity	NPC180733
0.7476	Intermediate Similarity	NPC291785
0.7476	Intermediate Similarity	NPC127408
0.7476	Intermediate Similarity	NPC41971
0.7474	Intermediate Similarity	NPC219535
0.7474	Intermediate Similarity	NPC34984
0.7474	Intermediate Similarity	NPC237938
0.7474	Intermediate Similarity	NPC65133
0.7474	Intermediate Similarity	NPC25037
0.7474	Intermediate Similarity	NPC291310

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 NPC17336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	497
0.1-0.2	3870
0.2-0.3	3216
0.3-0.4	908
0.4-0.5	337
0.5-0.6	215
0.6-0.7	104
0.7-0.8	3
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
0.7745	Intermediate Similarity	NPD1700	Approved
0.7477	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3703	Phase 2
0.7204	Intermediate Similarity	NPD6697	Approved
0.7204	Intermediate Similarity	NPD6118	Approved
0.7204	Intermediate Similarity	NPD6115	Approved
0.7204	Intermediate Similarity	NPD6114	Approved
0.7196	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6116	Phase 1
0.6989	Remote Similarity	NPD6117	Approved
0.6937	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6319	Approved
0.678	Remote Similarity	NPD6054	Approved
0.678	Remote Similarity	NPD6059	Approved
0.6778	Remote Similarity	NPD5360	Phase 3
0.6778	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4634	Approved
0.6723	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6370	Approved
0.663	Remote Similarity	NPD4244	Approved
0.663	Remote Similarity	NPD4245	Approved
0.663	Remote Similarity	NPD4789	Approved
0.6583	Remote Similarity	NPD6015	Approved
0.6583	Remote Similarity	NPD6016	Approved
0.6557	Remote Similarity	NPD7492	Approved
0.6552	Remote Similarity	NPD4632	Approved
0.6529	Remote Similarity	NPD5988	Approved
0.6526	Remote Similarity	NPD3702	Approved
0.6522	Remote Similarity	NPD3698	Phase 2
0.6518	Remote Similarity	NPD6675	Approved
0.6518	Remote Similarity	NPD6008	Approved
0.6518	Remote Similarity	NPD6402	Approved
0.6518	Remote Similarity	NPD7128	Approved
0.6518	Remote Similarity	NPD5739	Approved
0.6517	Remote Similarity	NPD371	Approved
0.6504	Remote Similarity	NPD6616	Approved
0.6491	Remote Similarity	NPD6373	Approved
0.6491	Remote Similarity	NPD6372	Approved
0.6491	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4755	Approved
0.648	Remote Similarity	NPD7319	Approved
0.6476	Remote Similarity	NPD8034	Phase 2
0.6476	Remote Similarity	NPD8035	Phase 2
0.6475	Remote Similarity	NPD7604	Phase 2
0.6466	Remote Similarity	NPD8297	Approved
0.646	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8293	Discontinued
0.6452	Remote Similarity	NPD7078	Approved
0.6442	Remote Similarity	NPD5328	Approved
0.6404	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD6899	Approved
0.6404	Remote Similarity	NPD7320	Approved
0.64	Remote Similarity	NPD7736	Approved
0.6387	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4758	Discontinued
0.6379	Remote Similarity	NPD6649	Approved
0.6379	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6327	Remote Similarity	NPD5364	Discontinued
0.6327	Remote Similarity	NPD3671	Phase 1
0.6321	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD6412	Phase 2
0.6316	Remote Similarity	NPD5697	Approved
0.6293	Remote Similarity	NPD6883	Approved
0.6293	Remote Similarity	NPD7290	Approved
0.6293	Remote Similarity	NPD7102	Approved
0.6271	Remote Similarity	NPD8133	Approved
0.627	Remote Similarity	NPD6033	Approved
0.6262	Remote Similarity	NPD6399	Phase 3
0.6262	Remote Similarity	NPD8171	Discontinued
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD6009	Approved
0.624	Remote Similarity	NPD7507	Approved
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD4697	Phase 3
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6869	Approved
0.6214	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6081	Approved
0.6211	Remote Similarity	NPD5777	Approved
0.621	Remote Similarity	NPD8328	Phase 3
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6014	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.62	Remote Similarity	NPD6928	Phase 2
0.6195	Remote Similarity	NPD5174	Approved
0.6195	Remote Similarity	NPD5175	Approved
0.6186	Remote Similarity	NPD6882	Approved
0.6179	Remote Similarity	NPD5983	Phase 2
0.6167	Remote Similarity	NPD6940	Discontinued
0.6161	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD3618	Phase 1
0.614	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5141	Approved
0.6121	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD4786	Approved
0.6111	Remote Similarity	NPD6336	Discontinued
0.6111	Remote Similarity	NPD4202	Approved
0.6105	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7524	Approved
0.6091	Remote Similarity	NPD5221	Approved
0.6091	Remote Similarity	NPD5222	Approved
0.6091	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4767	Approved
0.6087	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD4754	Approved
0.6036	Remote Similarity	NPD5173	Approved
0.6022	Remote Similarity	NPD4224	Phase 2
0.6019	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD4238	Approved
0.5983	Remote Similarity	NPD4729	Approved
0.5983	Remote Similarity	NPD5128	Approved
0.5983	Remote Similarity	NPD4730	Approved
0.5982	Remote Similarity	NPD7638	Approved
0.598	Remote Similarity	NPD1779	Approved
0.598	Remote Similarity	NPD1780	Approved
0.5938	Remote Similarity	NPD4787	Phase 1
0.5929	Remote Similarity	NPD7639	Approved
0.5929	Remote Similarity	NPD8418	Phase 2
0.5929	Remote Similarity	NPD7640	Approved
0.5922	Remote Similarity	NPD3667	Approved
0.5902	Remote Similarity	NPD6274	Approved
0.5893	Remote Similarity	NPD6083	Phase 2
0.5893	Remote Similarity	NPD6084	Phase 2
0.5887	Remote Similarity	NPD7101	Approved
0.5887	Remote Similarity	NPD7516	Approved
0.5887	Remote Similarity	NPD7100	Approved
0.5882	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD5250	Approved
0.5882	Remote Similarity	NPD5249	Phase 3
0.5882	Remote Similarity	NPD5248	Approved
0.5882	Remote Similarity	NPD7525	Registered
0.5882	Remote Similarity	NPD5247	Approved
0.5882	Remote Similarity	NPD5251	Approved
0.5865	Remote Similarity	NPD3669	Approved
0.5865	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4225	Approved
0.5833	Remote Similarity	NPD5215	Approved
0.5833	Remote Similarity	NPD5217	Approved
0.5833	Remote Similarity	NPD5216	Approved
0.5833	Remote Similarity	NPD4753	Phase 2
0.5826	Remote Similarity	NPD8138	Approved
0.5826	Remote Similarity	NPD8083	Approved
0.5826	Remote Similarity	NPD8084	Approved
0.5826	Remote Similarity	NPD8139	Approved
0.5826	Remote Similarity	NPD8085	Approved
0.5826	Remote Similarity	NPD8086	Approved
0.5826	Remote Similarity	NPD8082	Approved
0.5826	Remote Similarity	NPD7632	Discontinued
0.5812	Remote Similarity	NPD6920	Discontinued
0.581	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7327	Approved
0.5806	Remote Similarity	NPD6335	Approved
0.5806	Remote Similarity	NPD7328	Approved
0.5794	Remote Similarity	NPD6908	Approved
0.5794	Remote Similarity	NPD6909	Approved
0.5776	Remote Similarity	NPD8275	Approved
0.5776	Remote Similarity	NPD8276	Approved
0.5752	Remote Similarity	NPD7902	Approved
0.575	Remote Similarity	NPD5135	Approved
0.575	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.575	Remote Similarity	NPD5169	Approved
0.5739	Remote Similarity	NPD4159	Approved
0.5739	Remote Similarity	NPD5344	Discontinued
0.5727	Remote Similarity	NPD7637	Suspended
0.5726	Remote Similarity	NPD6317	Approved
0.5726	Remote Similarity	NPD8081	Approved
0.5714	Remote Similarity	NPD6686	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD6695	Phase 3
0.5714	Remote Similarity	NPD5210	Approved
0.5703	Remote Similarity	NPD6067	Discontinued
0.5702	Remote Similarity	NPD5127	Approved
0.5702	Remote Similarity	NPD5696	Approved
0.568	Remote Similarity	NPD6313	Approved
0.568	Remote Similarity	NPD6314	Approved
0.5678	Remote Similarity	NPD8393	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