NPASS Compound

Structure

NPC276103 OpenBabel07101719132D 36 40 0 0 1 0 0 0 0 0999 V2000 4.6199 0.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9257 0.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0303 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0357 -1.1533 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2925 -1.8224 0.0000 C 0 0 0 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 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5983 -2.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8767 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0846 -0.8443 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 2 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3904 -1.2044 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 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 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3415 -1.5134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 20 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 30 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 21 2 0 0 0 0 14 27 1 0 0 0 0 15 25 1 0 0 0 0 15 28 1 0 0 0 0 16 26 1 0 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 18 3 1 6 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 4 1 1 0 0 0 19 31 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 30 1 0 0 0 0 22 34 1 1 0 0 0 23 32 1 1 0 0 0 24 29 1 0 0 0 0 24 32 1 1 0 0 0 25 29 1 0 0 0 0 25 30 1 1 0 0 0 26 31 1 6 0 0 0 27 29 1 0 0 0 0 27 35 1 6 0 0 0 28 32 1 1 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.39
Volume:	549.134
LogP:	5.18
LogD:	5.413
LogS:	-4.885
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	5.231
Fsp3:	0.906
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-4.753
MDCK Permeability:	5.463909837999381e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.482
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.214
30% Bioavailability (F30%):	0.57

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	92.36539459228516%
Volume Distribution (VD):	1.023
Pgp-substrate:	2.296948194503784%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.245
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.418
CYP3A4-substrate:	0.641

ADMET: Excretion

Clearance (CL):	5.214
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.559
Skin Sensitization:	0.134
Carcinogencity:	0.006
Eye Corrosion:	0.035
Eye Irritation:	0.107
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC276103

Natural Product ID:	NPC276103
*Common Name:**	12Beta-Acetoxy-7Alpha-Hydroxygorgosterol
IUPAC Name:	[(3S,7S,8R,9S,10R,12R,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-17-[(1R)-1-[(1R,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
Synonyms:
Standard InCHIKey:	CUYULTOZWPGDFW-OZYXUASZSA-N
Standard InCHI:	InChI=1S/C32H52O4/c1-17(2)19(4)31(7)16-26(31)18(3)23-9-10-24-29-25(15-28(32(23,24)8)36-20(5)33)30(6)12-11-22(34)13-21(30)14-27(29)35/h14,17-19,22-29,34-35H,9-13,15-16H2,1-8H3/t18-,19+,22-,23+,24-,25-,26+,27+,28+,29-,30-,31+,32+/m0/s1
SMILES:	CC(C)[C@@H](C)[C@@]1(C)C[C@@H]1[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H]([C@]12C)OC(=O)C)[C@@]1(C)CC[C@@H](CC1=C[C@H]3O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454512
PubChem CID:	637179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002039] Gorgostanes 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
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608844]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	1.0	mm	PMID[489547]
NPT1232	Organism	Eurotium repens	Eurotium repens	IZ	=	2.0	mm	PMID[489547]

☑ 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 NPC276103 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	182
0.1-0.2	1314
0.2-0.3	4548
0.3-0.4	12482
0.4-0.5	9836
0.5-0.6	5901
0.6-0.7	5721
0.7-0.8	2492
0.8-0.85	183
0.85-0.9	34
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54248
0.9556	High Similarity	NPC474922
0.9121	High Similarity	NPC234335
0.8989	High Similarity	NPC474970
0.8936	High Similarity	NPC253115
0.8936	High Similarity	NPC304899
0.8878	High Similarity	NPC473543
0.8866	High Similarity	NPC476471
0.8866	High Similarity	NPC475344
0.8817	High Similarity	NPC38232
0.8776	High Similarity	NPC474124
0.8776	High Similarity	NPC473523
0.8763	High Similarity	NPC475617
0.875	High Similarity	NPC300179
0.875	High Similarity	NPC102426
0.8723	High Similarity	NPC279410
0.8723	High Similarity	NPC476186
0.8723	High Similarity	NPC119562
0.871	High Similarity	NPC177641
0.866	High Similarity	NPC208358
0.8646	High Similarity	NPC141401
0.8646	High Similarity	NPC475032
0.8646	High Similarity	NPC475033
0.8617	High Similarity	NPC476304
0.8614	High Similarity	NPC472219
0.8614	High Similarity	NPC472218
0.8614	High Similarity	NPC472217
0.8602	High Similarity	NPC295668
0.8586	High Similarity	NPC85742
0.8571	High Similarity	NPC261266
0.8571	High Similarity	NPC155974
0.8571	High Similarity	NPC6391
0.8571	High Similarity	NPC289670
0.8557	High Similarity	NPC247233
0.8556	High Similarity	NPC102048
0.8511	High Similarity	NPC110923
0.8511	High Similarity	NPC74296
0.8495	Intermediate Similarity	NPC246028
0.8495	Intermediate Similarity	NPC262858
0.8495	Intermediate Similarity	NPC146554
0.8495	Intermediate Similarity	NPC472240
0.8495	Intermediate Similarity	NPC16265
0.8469	Intermediate Similarity	NPC473510
0.8469	Intermediate Similarity	NPC251680
0.8454	Intermediate Similarity	NPC99726
0.8444	Intermediate Similarity	NPC139206
0.8438	Intermediate Similarity	NPC279974
0.8427	Intermediate Similarity	NPC209620
0.8427	Intermediate Similarity	NPC23852
0.8421	Intermediate Similarity	NPC473678
0.8404	Intermediate Similarity	NPC471896
0.84	Intermediate Similarity	NPC222153
0.84	Intermediate Similarity	NPC36688
0.8387	Intermediate Similarity	NPC470613
0.8387	Intermediate Similarity	NPC470612
0.8384	Intermediate Similarity	NPC295110
0.8384	Intermediate Similarity	NPC25177
0.8384	Intermediate Similarity	NPC247701
0.8384	Intermediate Similarity	NPC222875
0.8384	Intermediate Similarity	NPC268829
0.837	Intermediate Similarity	NPC168231
0.837	Intermediate Similarity	NPC477668
0.8367	Intermediate Similarity	NPC218107
0.8367	Intermediate Similarity	NPC119036
0.8352	Intermediate Similarity	NPC474047
0.8352	Intermediate Similarity	NPC299963
0.8351	Intermediate Similarity	NPC114743
0.8351	Intermediate Similarity	NPC88009
0.8351	Intermediate Similarity	NPC195366
0.8351	Intermediate Similarity	NPC72204
0.8333	Intermediate Similarity	NPC475781
0.8333	Intermediate Similarity	NPC101462
0.8333	Intermediate Similarity	NPC50964
0.8333	Intermediate Similarity	NPC472504
0.8316	Intermediate Similarity	NPC477574
0.8316	Intermediate Similarity	NPC41239
0.8316	Intermediate Similarity	NPC26888
0.8298	Intermediate Similarity	NPC473647
0.8283	Intermediate Similarity	NPC161527
0.8283	Intermediate Similarity	NPC219285
0.8283	Intermediate Similarity	NPC477972
0.8283	Intermediate Similarity	NPC230546
0.8283	Intermediate Similarity	NPC228251
0.8283	Intermediate Similarity	NPC477971
0.8283	Intermediate Similarity	NPC20113
0.8283	Intermediate Similarity	NPC477968
0.8265	Intermediate Similarity	NPC320306
0.8265	Intermediate Similarity	NPC210337
0.8261	Intermediate Similarity	NPC266511
0.8247	Intermediate Similarity	NPC476894
0.8247	Intermediate Similarity	NPC84383
0.8242	Intermediate Similarity	NPC475789
0.8242	Intermediate Similarity	NPC477667
0.8235	Intermediate Similarity	NPC119855
0.8235	Intermediate Similarity	NPC278628
0.8235	Intermediate Similarity	NPC470056
0.8235	Intermediate Similarity	NPC220217
0.8235	Intermediate Similarity	NPC231530
0.8235	Intermediate Similarity	NPC470055
0.8229	Intermediate Similarity	NPC26046
0.8229	Intermediate Similarity	NPC477855
0.8229	Intermediate Similarity	NPC214697
0.8229	Intermediate Similarity	NPC27918
0.8222	Intermediate Similarity	NPC142163
0.8218	Intermediate Similarity	NPC297617
0.8218	Intermediate Similarity	NPC10232
0.8218	Intermediate Similarity	NPC196471
0.8218	Intermediate Similarity	NPC476237
0.8218	Intermediate Similarity	NPC475334
0.8218	Intermediate Similarity	NPC160583
0.8218	Intermediate Similarity	NPC473694
0.8218	Intermediate Similarity	NPC189588
0.8218	Intermediate Similarity	NPC187302
0.8218	Intermediate Similarity	NPC97487
0.8218	Intermediate Similarity	NPC475623
0.8211	Intermediate Similarity	NPC148414
0.8211	Intermediate Similarity	NPC10274
0.8211	Intermediate Similarity	NPC48732
0.8211	Intermediate Similarity	NPC111585
0.8211	Intermediate Similarity	NPC78973
0.8211	Intermediate Similarity	NPC219937
0.8211	Intermediate Similarity	NPC175628
0.8211	Intermediate Similarity	NPC220216
0.8211	Intermediate Similarity	NPC123252
0.8211	Intermediate Similarity	NPC194485
0.8211	Intermediate Similarity	NPC53890
0.8202	Intermediate Similarity	NPC30986
0.8202	Intermediate Similarity	NPC209430
0.8202	Intermediate Similarity	NPC28862
0.8202	Intermediate Similarity	NPC84694
0.8202	Intermediate Similarity	NPC44083
0.8202	Intermediate Similarity	NPC47982
0.8202	Intermediate Similarity	NPC81306
0.8202	Intermediate Similarity	NPC143182
0.8202	Intermediate Similarity	NPC153987
0.8202	Intermediate Similarity	NPC109546
0.82	Intermediate Similarity	NPC96784
0.82	Intermediate Similarity	NPC235920
0.82	Intermediate Similarity	NPC75941
0.8191	Intermediate Similarity	NPC160304
0.8191	Intermediate Similarity	NPC67872
0.8191	Intermediate Similarity	NPC474668
0.819	Intermediate Similarity	NPC470076
0.8182	Intermediate Similarity	NPC275086
0.8182	Intermediate Similarity	NPC470066
0.8182	Intermediate Similarity	NPC470068
0.8182	Intermediate Similarity	NPC325229
0.8182	Intermediate Similarity	NPC470067
0.8173	Intermediate Similarity	NPC472216
0.8173	Intermediate Similarity	NPC284828
0.8173	Intermediate Similarity	NPC173905
0.8173	Intermediate Similarity	NPC5475
0.8172	Intermediate Similarity	NPC293287
0.8172	Intermediate Similarity	NPC152808
0.8172	Intermediate Similarity	NPC94462
0.8163	Intermediate Similarity	NPC7124
0.8163	Intermediate Similarity	NPC471903
0.8163	Intermediate Similarity	NPC475178
0.8163	Intermediate Similarity	NPC327788
0.8152	Intermediate Similarity	NPC205845
0.8152	Intermediate Similarity	NPC124172
0.8152	Intermediate Similarity	NPC185568
0.8144	Intermediate Similarity	NPC469406
0.8144	Intermediate Similarity	NPC105490
0.8144	Intermediate Similarity	NPC472360
0.8144	Intermediate Similarity	NPC472416
0.8144	Intermediate Similarity	NPC144202
0.8137	Intermediate Similarity	NPC31430
0.8137	Intermediate Similarity	NPC475331
0.8137	Intermediate Similarity	NPC85593
0.8137	Intermediate Similarity	NPC75608
0.8137	Intermediate Similarity	NPC475335
0.8137	Intermediate Similarity	NPC181104
0.8137	Intermediate Similarity	NPC201144
0.8137	Intermediate Similarity	NPC80809
0.8137	Intermediate Similarity	NPC121518
0.8137	Intermediate Similarity	NPC152966
0.8137	Intermediate Similarity	NPC103298
0.8137	Intermediate Similarity	NPC288502
0.8132	Intermediate Similarity	NPC470049
0.8132	Intermediate Similarity	NPC256112
0.8132	Intermediate Similarity	NPC49964
0.8125	Intermediate Similarity	NPC212948
0.8125	Intermediate Similarity	NPC124374
0.8125	Intermediate Similarity	NPC41554
0.8125	Intermediate Similarity	NPC97404
0.8119	Intermediate Similarity	NPC136289
0.8111	Intermediate Similarity	NPC234193
0.8105	Intermediate Similarity	NPC475921
0.8105	Intermediate Similarity	NPC477917
0.8105	Intermediate Similarity	NPC170633
0.8105	Intermediate Similarity	NPC474704
0.8105	Intermediate Similarity	NPC470361
0.8105	Intermediate Similarity	NPC261320
0.8105	Intermediate Similarity	NPC128496
0.8105	Intermediate Similarity	NPC314727
0.8105	Intermediate Similarity	NPC474889
0.81	Intermediate Similarity	NPC470074
0.81	Intermediate Similarity	NPC266955
0.81	Intermediate Similarity	NPC327431

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 NPC276103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1480
0.2-0.3	3981
0.3-0.4	2429
0.4-0.5	614
0.5-0.6	220
0.6-0.7	216
0.7-0.8	61
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
0.8469	Intermediate Similarity	NPD7640	Approved
0.8469	Intermediate Similarity	NPD7639	Approved
0.8367	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.7767	Intermediate Similarity	NPD7632	Discontinued
0.7755	Intermediate Similarity	NPD7637	Suspended
0.7753	Intermediate Similarity	NPD7339	Approved
0.7753	Intermediate Similarity	NPD6942	Approved
0.7717	Intermediate Similarity	NPD7525	Registered
0.7708	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6695	Phase 3
0.7579	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4786	Approved
0.7551	Intermediate Similarity	NPD6051	Approved
0.7526	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD7115	Discovery
0.7473	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6902	Approved
0.7426	Intermediate Similarity	NPD7748	Approved
0.7419	Intermediate Similarity	NPD6929	Approved
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD8034	Phase 2
0.7391	Intermediate Similarity	NPD8033	Approved
0.7383	Intermediate Similarity	NPD6008	Approved
0.7383	Intermediate Similarity	NPD7128	Approved
0.7383	Intermediate Similarity	NPD6675	Approved
0.7383	Intermediate Similarity	NPD6402	Approved
0.7383	Intermediate Similarity	NPD5739	Approved
0.7374	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD3667	Approved
0.7347	Intermediate Similarity	NPD7524	Approved
0.734	Intermediate Similarity	NPD6930	Phase 2
0.734	Intermediate Similarity	NPD6931	Approved
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD8377	Approved
0.7304	Intermediate Similarity	NPD8294	Approved
0.7281	Intermediate Similarity	NPD7327	Approved
0.7281	Intermediate Similarity	NPD7328	Approved
0.7248	Intermediate Similarity	NPD7320	Approved
0.7248	Intermediate Similarity	NPD6899	Approved
0.7248	Intermediate Similarity	NPD6881	Approved
0.7245	Intermediate Similarity	NPD3618	Phase 1
0.7241	Intermediate Similarity	NPD8380	Approved
0.7241	Intermediate Similarity	NPD8378	Approved
0.7241	Intermediate Similarity	NPD8379	Approved
0.7241	Intermediate Similarity	NPD8335	Approved
0.7241	Intermediate Similarity	NPD8296	Approved
0.7234	Intermediate Similarity	NPD7645	Phase 2
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7228	Intermediate Similarity	NPD6079	Approved
0.7217	Intermediate Similarity	NPD7516	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7212	Intermediate Similarity	NPD7902	Approved
0.7207	Intermediate Similarity	NPD8130	Phase 1
0.7204	Intermediate Similarity	NPD5776	Phase 2
0.7204	Intermediate Similarity	NPD6925	Approved
0.7184	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6372	Approved
0.7182	Intermediate Similarity	NPD6373	Approved
0.7158	Intermediate Similarity	NPD7514	Phase 3
0.7156	Intermediate Similarity	NPD5701	Approved
0.7156	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7128	Intermediate Similarity	NPD7145	Approved
0.7119	Intermediate Similarity	NPD7604	Phase 2
0.7117	Intermediate Similarity	NPD7290	Approved
0.7117	Intermediate Similarity	NPD6883	Approved
0.7117	Intermediate Similarity	NPD7102	Approved
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.7094	Intermediate Similarity	NPD7503	Approved
0.7091	Intermediate Similarity	NPD6011	Approved
0.708	Intermediate Similarity	NPD4632	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7065	Intermediate Similarity	NPD6926	Approved
0.7065	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD7087	Discontinued
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6617	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD6847	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD5344	Discontinued
0.6991	Remote Similarity	NPD6882	Approved
0.699	Remote Similarity	NPD5779	Approved
0.699	Remote Similarity	NPD4202	Approved
0.699	Remote Similarity	NPD5778	Approved
0.6989	Remote Similarity	NPD8264	Approved
0.6979	Remote Similarity	NPD7332	Phase 2
0.697	Remote Similarity	NPD6893	Approved
0.6952	Remote Similarity	NPD5221	Approved
0.6952	Remote Similarity	NPD4697	Phase 3
0.6952	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5222	Approved
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7900	Approved
0.6915	Remote Similarity	NPD6933	Approved
0.6897	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD5173	Approved
0.6887	Remote Similarity	NPD4755	Approved
0.6882	Remote Similarity	NPD4784	Approved
0.6882	Remote Similarity	NPD4785	Approved
0.6869	Remote Similarity	NPD3665	Phase 1
0.6869	Remote Similarity	NPD3133	Approved
0.6869	Remote Similarity	NPD3666	Approved
0.6869	Remote Similarity	NPD3668	Phase 3
0.6864	Remote Similarity	NPD6319	Approved
0.686	Remote Similarity	NPD7507	Approved
0.6857	Remote Similarity	NPD5695	Phase 3
0.6848	Remote Similarity	NPD7152	Approved
0.6848	Remote Similarity	NPD7150	Approved
0.6848	Remote Similarity	NPD4243	Approved
0.6848	Remote Similarity	NPD7151	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6842	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6932	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6923	Approved
0.6813	Remote Similarity	NPD6922	Approved
0.681	Remote Similarity	NPD6868	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6804	Remote Similarity	NPD4748	Discontinued
0.6803	Remote Similarity	NPD8293	Discontinued
0.6786	Remote Similarity	NPD6686	Approved
0.6777	Remote Similarity	NPD7492	Approved
0.6771	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5362	Discontinued
0.6762	Remote Similarity	NPD6001	Approved
0.6759	Remote Similarity	NPD6648	Approved
0.6759	Remote Similarity	NPD4700	Approved
0.6759	Remote Similarity	NPD5286	Approved
0.6759	Remote Similarity	NPD4696	Approved
0.6759	Remote Similarity	NPD5285	Approved
0.6748	Remote Similarity	NPD7736	Approved
0.6739	Remote Similarity	NPD7144	Approved
0.6739	Remote Similarity	NPD7143	Approved
0.6737	Remote Similarity	NPD6117	Approved
0.6735	Remote Similarity	NPD6898	Phase 1
0.6733	Remote Similarity	NPD6098	Approved
0.6731	Remote Similarity	NPD6411	Approved
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6054	Approved
0.6723	Remote Similarity	NPD6059	Approved
0.6721	Remote Similarity	NPD6336	Discontinued
0.6721	Remote Similarity	NPD6616	Approved
0.6701	Remote Similarity	NPD6683	Phase 2
0.6701	Remote Similarity	NPD4195	Approved
0.67	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6699	Remote Similarity	NPD4753	Phase 2
0.6697	Remote Similarity	NPD5223	Approved
0.6695	Remote Similarity	NPD6335	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6638	Remote Similarity	NPD8133	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7509	Discontinued
0.6612	Remote Similarity	NPD6370	Approved
0.661	Remote Similarity	NPD6317	Approved
0.66	Remote Similarity	NPD5332	Approved
0.66	Remote Similarity	NPD5331	Approved
0.6577	Remote Similarity	NPD5174	Approved
0.6577	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD4754	Approved
0.6571	Remote Similarity	NPD5693	Phase 1
0.6569	Remote Similarity	NPD4249	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