NPASS Compound

Structure

NPC475032 OpenBabel07101718282D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -0.9000 2.9543 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 1.7321 -3.0000 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 4.3301 -1.5000 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 3.4641 -3.0000 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 -2.1871 4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 3.1622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 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 2.5981 -2.5000 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 0.8660 -1.5000 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 -1.5388 -0.5000 0.0000 C 0 0 3 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 1.7321 -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 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 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 -2.5388 -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 1.5000 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 5 19 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 29 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 6 0 0 0 18 4 1 6 0 0 0 18 25 1 0 0 0 0 19 31 2 0 0 0 0 19 35 1 0 0 0 0 20 29 1 0 0 0 0 21 32 1 6 0 0 0 22 11 1 1 0 0 0 22 23 1 0 0 0 0 22 26 1 0 0 0 0 23 30 1 6 0 0 0 24 25 1 0 0 0 0 24 33 1 0 0 0 0 25 30 1 6 0 0 0 26 27 1 0 0 0 0 26 29 1 6 0 0 0 27 28 1 0 0 0 0 27 34 1 6 0 0 0 28 30 1 6 0 0 0 28 35 1 0 0 0 0 29 6 1 6 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	5.404
LogD:	4.782
LogS:	-4.665
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	5.165
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.677
MDCK Permeability:	3.906409983756021e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.846
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.247
Plasma Protein Binding (PPB):	95.83531951904297%
Volume Distribution (VD):	1.05
Pgp-substrate:	3.065817356109619%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.675
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.414
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	8.663
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.509
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.18
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.238
Carcinogencity:	0.337
Eye Corrosion:	0.025
Eye Irritation:	0.02
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC475032

Natural Product ID:	NPC475032
*Common Name:**	12Beta-Acetoxyergost-5-Ene-3Beta,11Beta,16-Triol
IUPAC Name:	[(3S,8S,9S,10R,11R,12S,13S,14S,17R)-17-[(2R,5S)-5,6-dimethylheptan-2-yl]-3,11,16-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
Synonyms:
Standard InCHIKey:	NLHKKMMSHLDPKW-MXORTOAHSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-16(2)17(3)8-9-18(4)25-24(33)15-23-22-11-10-20-14-21(32)12-13-29(20,6)26(22)27(34)28(30(23,25)7)35-19(5)31/h10,16-18,21-28,32-34H,8-9,11-15H2,1-7H3/t17-,18+,21-,22-,23-,24?,25-,26+,27+,28+,29-,30-/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@H](O)[C@H]2[C@H]([C@H]3[C@@]1(C)[C@@H]([C@@H](CC[C@@H](C(C)C)C)C)C(C3)O)CC=C1[C@]2(C)CC[C@@H](C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493433
PubChem CID:	44566214
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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	1

Activity Type	# Activity
Organism	1

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[519946]

☑ 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 NPC475032 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	183
0.1-0.2	1277
0.2-0.3	4783
0.3-0.4	12167
0.4-0.5	9789
0.5-0.6	5432
0.6-0.7	5449
0.7-0.8	3300
0.8-0.85	275
0.85-0.9	33
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475033
0.9677	High Similarity	NPC155974
0.957	High Similarity	NPC208358
0.9263	High Similarity	NPC475617
0.9247	High Similarity	NPC304899
0.9247	High Similarity	NPC253115
0.9072	High Similarity	NPC474124
0.9043	High Similarity	NPC475178
0.8969	High Similarity	NPC476471
0.8969	High Similarity	NPC475344
0.8889	High Similarity	NPC474970
0.8854	High Similarity	NPC300179
0.8854	High Similarity	NPC102426
0.8842	High Similarity	NPC471903
0.8842	High Similarity	NPC88009
0.8804	High Similarity	NPC105495
0.8788	High Similarity	NPC473543
0.8788	High Similarity	NPC152966
0.8763	High Similarity	NPC473510
0.875	High Similarity	NPC210337
0.8723	High Similarity	NPC473678
0.8696	High Similarity	NPC470613
0.8696	High Similarity	NPC470612
0.8687	High Similarity	NPC473523
0.8673	High Similarity	NPC289670
0.8667	High Similarity	NPC124172
0.866	High Similarity	NPC470068
0.866	High Similarity	NPC470067
0.866	High Similarity	NPC470066
0.8654	High Similarity	NPC144068
0.8646	High Similarity	NPC169270
0.8646	High Similarity	NPC306797
0.8646	High Similarity	NPC276103
0.8646	High Similarity	NPC111834
0.8646	High Similarity	NPC292718
0.8646	High Similarity	NPC54248
0.8641	High Similarity	NPC114188
0.8632	High Similarity	NPC474922
0.8617	High Similarity	NPC210268
0.8617	High Similarity	NPC219516
0.8617	High Similarity	NPC234335
0.8602	High Similarity	NPC473647
0.86	High Similarity	NPC85593
0.86	High Similarity	NPC31430
0.8586	High Similarity	NPC154452
0.8571	High Similarity	NPC230546
0.8557	High Similarity	NPC274793
0.8542	High Similarity	NPC241047
0.8529	High Similarity	NPC295980
0.8526	High Similarity	NPC98193
0.8515	High Similarity	NPC278628
0.8515	High Similarity	NPC231530
0.8515	High Similarity	NPC186668
0.85	High Similarity	NPC475334
0.85	High Similarity	NPC475701
0.85	High Similarity	NPC475623
0.85	High Similarity	NPC472821
0.85	High Similarity	NPC473694
0.8495	Intermediate Similarity	NPC475664
0.8485	Intermediate Similarity	NPC476132
0.8485	Intermediate Similarity	NPC144486
0.8485	Intermediate Similarity	NPC21064
0.8485	Intermediate Similarity	NPC470054
0.8485	Intermediate Similarity	NPC121072
0.8478	Intermediate Similarity	NPC24277
0.8469	Intermediate Similarity	NPC247233
0.8469	Intermediate Similarity	NPC477876
0.8469	Intermediate Similarity	NPC477875
0.8469	Intermediate Similarity	NPC469725
0.8444	Intermediate Similarity	NPC470614
0.8444	Intermediate Similarity	NPC1272
0.8421	Intermediate Similarity	NPC189520
0.8416	Intermediate Similarity	NPC201144
0.8416	Intermediate Similarity	NPC474464
0.8416	Intermediate Similarity	NPC288502
0.8416	Intermediate Similarity	NPC474550
0.8416	Intermediate Similarity	NPC475335
0.8416	Intermediate Similarity	NPC475585
0.8416	Intermediate Similarity	NPC475331
0.8416	Intermediate Similarity	NPC181104
0.8416	Intermediate Similarity	NPC473577
0.8416	Intermediate Similarity	NPC80809
0.8416	Intermediate Similarity	NPC103298
0.8416	Intermediate Similarity	NPC121518
0.84	Intermediate Similarity	NPC31085
0.84	Intermediate Similarity	NPC22388
0.84	Intermediate Similarity	NPC470053
0.84	Intermediate Similarity	NPC177701
0.8387	Intermediate Similarity	NPC474657
0.8387	Intermediate Similarity	NPC186145
0.8384	Intermediate Similarity	NPC167974
0.8384	Intermediate Similarity	NPC474571
0.8384	Intermediate Similarity	NPC254567
0.8384	Intermediate Similarity	NPC471242
0.8384	Intermediate Similarity	NPC476195
0.8381	Intermediate Similarity	NPC280782
0.8352	Intermediate Similarity	NPC110778
0.835	Intermediate Similarity	NPC472219
0.835	Intermediate Similarity	NPC472218
0.835	Intermediate Similarity	NPC472217
0.835	Intermediate Similarity	NPC94529
0.835	Intermediate Similarity	NPC88701
0.8333	Intermediate Similarity	NPC220217
0.8333	Intermediate Similarity	NPC470375
0.8333	Intermediate Similarity	NPC470055
0.8333	Intermediate Similarity	NPC119855
0.8333	Intermediate Similarity	NPC242748
0.8333	Intermediate Similarity	NPC470056
0.8333	Intermediate Similarity	NPC475290
0.8333	Intermediate Similarity	NPC474531
0.8333	Intermediate Similarity	NPC474015
0.8333	Intermediate Similarity	NPC470376
0.8333	Intermediate Similarity	NPC60315
0.8333	Intermediate Similarity	NPC26046
0.8333	Intermediate Similarity	NPC473199
0.8317	Intermediate Similarity	NPC471467
0.8317	Intermediate Similarity	NPC160583
0.8317	Intermediate Similarity	NPC140723
0.8316	Intermediate Similarity	NPC194485
0.8316	Intermediate Similarity	NPC53890
0.8316	Intermediate Similarity	NPC219937
0.8316	Intermediate Similarity	NPC123252
0.8316	Intermediate Similarity	NPC475751
0.8316	Intermediate Similarity	NPC473956
0.8302	Intermediate Similarity	NPC962
0.8302	Intermediate Similarity	NPC250109
0.83	Intermediate Similarity	NPC96784
0.83	Intermediate Similarity	NPC222875
0.83	Intermediate Similarity	NPC25177
0.83	Intermediate Similarity	NPC235920
0.83	Intermediate Similarity	NPC295110
0.83	Intermediate Similarity	NPC268829
0.83	Intermediate Similarity	NPC49532
0.83	Intermediate Similarity	NPC247701
0.8298	Intermediate Similarity	NPC160304
0.8298	Intermediate Similarity	NPC470542
0.8298	Intermediate Similarity	NPC474668
0.8286	Intermediate Similarity	NPC263827
0.8286	Intermediate Similarity	NPC250481
0.8286	Intermediate Similarity	NPC285410
0.8286	Intermediate Similarity	NPC470748
0.8283	Intermediate Similarity	NPC477854
0.8283	Intermediate Similarity	NPC309493
0.8283	Intermediate Similarity	NPC216260
0.8283	Intermediate Similarity	NPC477928
0.8283	Intermediate Similarity	NPC5358
0.828	Intermediate Similarity	NPC94462
0.828	Intermediate Similarity	NPC286153
0.8269	Intermediate Similarity	NPC125361
0.8269	Intermediate Similarity	NPC51925
0.8269	Intermediate Similarity	NPC154085
0.8269	Intermediate Similarity	NPC296761
0.8269	Intermediate Similarity	NPC5475
0.8269	Intermediate Similarity	NPC472216
0.8269	Intermediate Similarity	NPC173905
0.8269	Intermediate Similarity	NPC43976
0.8269	Intermediate Similarity	NPC284828
0.8265	Intermediate Similarity	NPC72204
0.8265	Intermediate Similarity	NPC173272
0.8261	Intermediate Similarity	NPC209802
0.8261	Intermediate Similarity	NPC127606
0.8261	Intermediate Similarity	NPC255882
0.8261	Intermediate Similarity	NPC475798
0.8261	Intermediate Similarity	NPC299963
0.8257	Intermediate Similarity	NPC475041
0.8252	Intermediate Similarity	NPC234160
0.8252	Intermediate Similarity	NPC475781
0.8252	Intermediate Similarity	NPC59530
0.8247	Intermediate Similarity	NPC211238
0.8247	Intermediate Similarity	NPC3359
0.8242	Intermediate Similarity	NPC472504
0.8241	Intermediate Similarity	NPC203862
0.8235	Intermediate Similarity	NPC470064
0.8235	Intermediate Similarity	NPC477812
0.8235	Intermediate Similarity	NPC470061
0.8235	Intermediate Similarity	NPC470057
0.8235	Intermediate Similarity	NPC471293
0.8235	Intermediate Similarity	NPC470058
0.8235	Intermediate Similarity	NPC470059
0.8235	Intermediate Similarity	NPC470060
0.8235	Intermediate Similarity	NPC471111
0.8235	Intermediate Similarity	NPC470043
0.8235	Intermediate Similarity	NPC470062
0.8229	Intermediate Similarity	NPC130840
0.8222	Intermediate Similarity	NPC26117
0.8222	Intermediate Similarity	NPC236112
0.8218	Intermediate Similarity	NPC470972
0.8211	Intermediate Similarity	NPC246028
0.8211	Intermediate Similarity	NPC109744
0.82	Intermediate Similarity	NPC317019
0.8191	Intermediate Similarity	NPC189777
0.819	Intermediate Similarity	NPC197428
0.819	Intermediate Similarity	NPC101450
0.8182	Intermediate Similarity	NPC177818
0.8182	Intermediate Similarity	NPC243728
0.8182	Intermediate Similarity	NPC471406
0.8182	Intermediate Similarity	NPC473890
0.8182	Intermediate Similarity	NPC473566
0.8182	Intermediate Similarity	NPC475358
0.8173	Intermediate Similarity	NPC472988

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 NPC475032 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1519
0.2-0.3	4093
0.3-0.4	2298
0.4-0.5	587
0.5-0.6	197
0.6-0.7	163
0.7-0.8	139
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.81	Intermediate Similarity	NPD7638	Approved
0.802	Intermediate Similarity	NPD7639	Approved
0.802	Intermediate Similarity	NPD7640	Approved
0.7963	Intermediate Similarity	NPD4632	Approved
0.7959	Intermediate Similarity	NPD6399	Phase 3
0.7928	Intermediate Similarity	NPD7516	Approved
0.7838	Intermediate Similarity	NPD7328	Approved
0.7838	Intermediate Similarity	NPD7327	Approved
0.7826	Intermediate Similarity	NPD7525	Registered
0.781	Intermediate Similarity	NPD5739	Approved
0.781	Intermediate Similarity	NPD6675	Approved
0.781	Intermediate Similarity	NPD7128	Approved
0.781	Intermediate Similarity	NPD6402	Approved
0.7788	Intermediate Similarity	NPD8033	Approved
0.7778	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6412	Phase 2
0.7706	Intermediate Similarity	NPD8297	Approved
0.7699	Intermediate Similarity	NPD8377	Approved
0.7699	Intermediate Similarity	NPD6319	Approved
0.7699	Intermediate Similarity	NPD8294	Approved
0.7667	Intermediate Similarity	NPD6942	Approved
0.7667	Intermediate Similarity	NPD7339	Approved
0.7664	Intermediate Similarity	NPD6881	Approved
0.7664	Intermediate Similarity	NPD7320	Approved
0.7664	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD6008	Approved
0.7632	Intermediate Similarity	NPD8379	Approved
0.7632	Intermediate Similarity	NPD8296	Approved
0.7632	Intermediate Similarity	NPD8378	Approved
0.7632	Intermediate Similarity	NPD8380	Approved
0.7632	Intermediate Similarity	NPD8335	Approved
0.7632	Intermediate Similarity	NPD7503	Approved
0.7629	Intermediate Similarity	NPD7524	Approved
0.7593	Intermediate Similarity	NPD6372	Approved
0.7593	Intermediate Similarity	NPD6373	Approved
0.7589	Intermediate Similarity	NPD6009	Approved
0.757	Intermediate Similarity	NPD5697	Approved
0.757	Intermediate Similarity	NPD5701	Approved
0.7523	Intermediate Similarity	NPD7102	Approved
0.7523	Intermediate Similarity	NPD7290	Approved
0.7523	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD7604	Phase 2
0.7478	Intermediate Similarity	NPD5983	Phase 2
0.7476	Intermediate Similarity	NPD6084	Phase 2
0.7476	Intermediate Similarity	NPD6083	Phase 2
0.7475	Intermediate Similarity	NPD6051	Approved
0.7455	Intermediate Similarity	NPD8130	Phase 1
0.7455	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6617	Approved
0.7455	Intermediate Similarity	NPD6650	Approved
0.7455	Intermediate Similarity	NPD6869	Approved
0.7455	Intermediate Similarity	NPD6649	Approved
0.7455	Intermediate Similarity	NPD6847	Approved
0.7449	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7492	Approved
0.7431	Intermediate Similarity	NPD6012	Approved
0.7431	Intermediate Similarity	NPD6013	Approved
0.7431	Intermediate Similarity	NPD6014	Approved
0.7426	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD6054	Approved
0.7391	Intermediate Similarity	NPD6059	Approved
0.7387	Intermediate Similarity	NPD6882	Approved
0.7373	Intermediate Similarity	NPD6336	Discontinued
0.7373	Intermediate Similarity	NPD6616	Approved
0.7373	Intermediate Similarity	NPD7507	Approved
0.7358	Intermediate Similarity	NPD7632	Discontinued
0.7347	Intermediate Similarity	NPD5330	Approved
0.7347	Intermediate Similarity	NPD7146	Approved
0.7347	Intermediate Similarity	NPD7521	Approved
0.7347	Intermediate Similarity	NPD7334	Approved
0.7347	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD6684	Approved
0.7327	Intermediate Similarity	NPD8034	Phase 2
0.7327	Intermediate Similarity	NPD8035	Phase 2
0.732	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7078	Approved
0.7311	Intermediate Similarity	NPD8293	Discontinued
0.7308	Intermediate Similarity	NPD4755	Approved
0.73	Intermediate Similarity	NPD5328	Approved
0.7292	Intermediate Similarity	NPD3667	Approved
0.7281	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD6370	Approved
0.725	Intermediate Similarity	NPD7736	Approved
0.7245	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4225	Approved
0.7216	Intermediate Similarity	NPD6695	Phase 3
0.7207	Intermediate Similarity	NPD4634	Approved
0.7204	Intermediate Similarity	NPD6933	Approved
0.72	Intermediate Similarity	NPD6903	Approved
0.72	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7319	Approved
0.7184	Intermediate Similarity	NPD7748	Approved
0.7179	Intermediate Similarity	NPD6016	Approved
0.7179	Intermediate Similarity	NPD6015	Approved
0.7174	Intermediate Similarity	NPD4785	Approved
0.7174	Intermediate Similarity	NPD4784	Approved
0.7172	Intermediate Similarity	NPD3618	Phase 1
0.717	Intermediate Similarity	NPD4696	Approved
0.717	Intermediate Similarity	NPD5286	Approved
0.717	Intermediate Similarity	NPD4700	Approved
0.717	Intermediate Similarity	NPD5285	Approved
0.7158	Intermediate Similarity	NPD7645	Phase 2
0.7157	Intermediate Similarity	NPD6079	Approved
0.7157	Intermediate Similarity	NPD7637	Suspended
0.7157	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD4243	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7119	Intermediate Similarity	NPD5988	Approved
0.7115	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5695	Phase 3
0.7103	Intermediate Similarity	NPD5223	Approved
0.7103	Intermediate Similarity	NPD5344	Discontinued
0.7083	Intermediate Similarity	NPD4748	Discontinued
0.7075	Intermediate Similarity	NPD5696	Approved
0.7069	Intermediate Similarity	NPD6335	Approved
0.7059	Intermediate Similarity	NPD6067	Discontinued
0.7043	Intermediate Similarity	NPD6274	Approved
0.7037	Intermediate Similarity	NPD5224	Approved
0.7037	Intermediate Similarity	NPD5211	Phase 2
0.7037	Intermediate Similarity	NPD5226	Approved
0.7037	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD4633	Approved
0.703	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6672	Approved
0.7027	Intermediate Similarity	NPD6686	Approved
0.7018	Intermediate Similarity	NPD8133	Approved
0.7009	Intermediate Similarity	NPD7101	Approved
0.7009	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD6098	Approved
0.6989	Remote Similarity	NPD6924	Approved
0.6989	Remote Similarity	NPD6926	Approved
0.6983	Remote Similarity	NPD6317	Approved
0.6979	Remote Similarity	NPD6929	Approved
0.6979	Remote Similarity	NPD4195	Approved
0.6972	Remote Similarity	NPD4754	Approved
0.6972	Remote Similarity	NPD5174	Approved
0.6972	Remote Similarity	NPD5175	Approved
0.6967	Remote Similarity	NPD6033	Approved
0.6961	Remote Similarity	NPD4753	Phase 2
0.6961	Remote Similarity	NPD6080	Approved
0.6961	Remote Similarity	NPD6904	Approved
0.6961	Remote Similarity	NPD6673	Approved
0.6944	Remote Similarity	NPD4159	Approved
0.6931	Remote Similarity	NPD7750	Discontinued
0.693	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD6314	Approved
0.6923	Remote Similarity	NPD6313	Approved
0.6909	Remote Similarity	NPD5141	Approved
0.6907	Remote Similarity	NPD6931	Approved
0.6907	Remote Similarity	NPD6930	Phase 2
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6909	Approved
0.6891	Remote Similarity	NPD6908	Approved
0.6887	Remote Similarity	NPD5222	Approved
0.6887	Remote Similarity	NPD4697	Phase 3
0.6887	Remote Similarity	NPD5221	Approved
0.6887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6115	Approved
0.6875	Remote Similarity	NPD6697	Approved
0.6875	Remote Similarity	NPD6118	Approved
0.6875	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6114	Approved
0.6857	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7900	Approved
0.6847	Remote Similarity	NPD4768	Approved
0.6847	Remote Similarity	NPD4767	Approved
0.6838	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5281	Approved
0.6827	Remote Similarity	NPD5284	Approved
0.6822	Remote Similarity	NPD5173	Approved
0.68	Remote Similarity	NPD3668	Phase 3
0.6777	Remote Similarity	NPD8328	Phase 3
0.6774	Remote Similarity	NPD7151	Approved
0.6774	Remote Similarity	NPD7150	Approved
0.6774	Remote Similarity	NPD7152	Approved
0.6771	Remote Similarity	NPD5776	Phase 2
0.6771	Remote Similarity	NPD6932	Approved
0.6771	Remote Similarity	NPD6116	Phase 1
0.6771	Remote Similarity	NPD6925	Approved
0.6768	Remote Similarity	NPD4223	Phase 3
0.6768	Remote Similarity	NPD4221	Approved
0.6752	Remote Similarity	NPD6868	Approved
0.675	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6922	Approved
0.6739	Remote Similarity	NPD6923	Approved
0.6737	Remote Similarity	NPD4190	Phase 3
0.6737	Remote Similarity	NPD5275	Approved
0.6735	Remote Similarity	NPD6928	Phase 2
0.6735	Remote Similarity	NPD7509	Discontinued
0.6733	Remote Similarity	NPD5329	Approved
0.6726	Remote Similarity	NPD4730	Approved
0.6726	Remote Similarity	NPD4729	Approved
0.6726	Remote Similarity	NPD5128	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