NPASS Compound

Structure

NPC471903 OpenBabel07101718302D 36 39 0 0 1 0 0 0 0 0999 V2000 4.8363 3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5636 4.8305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8215 8.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5939 6.6586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8018 5.6805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2109 4.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1910 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 3.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5417 5.0385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4906 7.6837 0.0000 C 0 0 0 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -0.8660 1.5000 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 1.8508 5.9895 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4688 7.8916 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 2.5000 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 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1816 6.7327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 19 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 8 9 2 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 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 20 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 0 0 0 0 17 1 1 1 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 18 27 1 0 0 0 0 19 31 2 0 0 0 0 19 36 1 0 0 0 0 20 32 1 1 0 0 0 21 15 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 24 29 1 1 0 0 0 25 29 1 1 0 0 0 25 33 1 0 0 0 0 26 30 1 1 0 0 0 26 34 1 0 0 0 0 27 36 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.36
Volume:	540.679
LogP:	4.602
LogD:	3.934
LogS:	-4.324
# Rotatable Bonds:	6
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	5.279
Fsp3:	0.9
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:	-4.843
MDCK Permeability:	9.410222992300987e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.3
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.477

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.401
Plasma Protein Binding (PPB):	89.26638793945312%
Volume Distribution (VD):	0.782
Pgp-substrate:	2.4842920303344727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.105
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	2.561
Half-life (T1/2):	0.246

ADMET: Toxicity

hERG Blockers:	0.48
Human Hepatotoxicity (H-HT):	0.707
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.922
Carcinogencity:	0.064
Eye Corrosion:	0.008
Eye Irritation:	0.053
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC471903

Natural Product ID:	NPC471903
*Common Name:**	(24S)-Ergost-22E-Ene-1Beta,3Beta,5Alpha,6Beta-Tetraol-25-Monoacetate
IUPAC Name:	[(E,3S,6R)-2,3-dimethyl-6-[(1R,3S,5R,6R,8S,9S,10S,13R,14S,17R)-1,3,5,6-tetrahydroxy-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]hept-4-en-2-yl] acetate
Synonyms:
Standard InCHIKey:	GMKVQEJYVZLMNA-UTTFFMQTSA-N
Standard InCHI:	InChI=1S/C30H50O6/c1-17(8-9-18(2)27(4,5)36-19(3)31)22-10-11-23-21-15-26(34)30(35)16-20(32)14-25(33)29(30,7)24(21)12-13-28(22,23)6/h8-9,17-18,20-26,32-35H,10-16H2,1-7H3/b9-8+/t17-,18+,20+,21+,22-,23+,24+,25-,26-,28-,29+,30+/m1/s1
SMILES:	CC(C=CC(C)C(C)(C)OC(=O)C)C1CCC2C1(CCC3C2CC(C4(C3(C(CC(C4)O)O)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289463
PubChem CID:	90681746
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
NPO32741	sarcophyton pauciplicatum	Species	Alcyoniidae	Eukaryota	n.a.	Vietnamese soft coral	n.a.	PMID[24852121]

☑ 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
EC50	1

Activity Type	# Activity
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	EC50	=	8270.0	nM	PMID[520661]

☑ 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 NPC471903 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	188
0.1-0.2	1287
0.2-0.3	4762
0.3-0.4	11975
0.4-0.5	10253
0.5-0.6	5487
0.6-0.7	5342
0.7-0.8	3150
0.8-0.85	213
0.85-0.9	36
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9121	High Similarity	NPC219516
0.9011	High Similarity	NPC473956
0.9011	High Similarity	NPC475751
0.8947	High Similarity	NPC300179
0.8947	High Similarity	NPC102426
0.8901	High Similarity	NPC109744
0.8854	High Similarity	NPC208358
0.8842	High Similarity	NPC475033
0.8842	High Similarity	NPC475032
0.8791	High Similarity	NPC475664
0.8763	High Similarity	NPC155974
0.8763	High Similarity	NPC289670
0.8763	High Similarity	NPC475617
0.875	High Similarity	NPC470067
0.875	High Similarity	NPC470066
0.875	High Similarity	NPC470068
0.8681	High Similarity	NPC474657
0.8681	High Similarity	NPC186145
0.8673	High Similarity	NPC477054
0.866	High Similarity	NPC473510
0.8646	High Similarity	NPC476040
0.8646	High Similarity	NPC476021
0.8646	High Similarity	NPC474994
0.8646	High Similarity	NPC210337
0.8646	High Similarity	NPC316604
0.8614	High Similarity	NPC472218
0.8614	High Similarity	NPC472217
0.8614	High Similarity	NPC472219
0.8602	High Similarity	NPC10274
0.8586	High Similarity	NPC474124
0.8586	High Similarity	NPC222153
0.8571	High Similarity	NPC474970
0.8571	High Similarity	NPC477051
0.8571	High Similarity	NPC477053
0.8571	High Similarity	NPC470054
0.8571	High Similarity	NPC6605
0.8571	High Similarity	NPC477052
0.8557	High Similarity	NPC477876
0.8557	High Similarity	NPC119036
0.8557	High Similarity	NPC477875
0.8542	High Similarity	NPC253115
0.8542	High Similarity	NPC304899
0.8542	High Similarity	NPC88009
0.8539	High Similarity	NPC202688
0.8539	High Similarity	NPC154043
0.8539	High Similarity	NPC60018
0.8529	High Similarity	NPC284828
0.8529	High Similarity	NPC5475
0.8529	High Similarity	NPC173905
0.8529	High Similarity	NPC472216
0.8511	High Similarity	NPC275671
0.8511	High Similarity	NPC97404
0.8511	High Similarity	NPC41554
0.85	High Similarity	NPC473543
0.8485	Intermediate Similarity	NPC475344
0.8485	Intermediate Similarity	NPC476471
0.8485	Intermediate Similarity	NPC470053
0.8469	Intermediate Similarity	NPC230546
0.8469	Intermediate Similarity	NPC317019
0.8454	Intermediate Similarity	NPC476893
0.8444	Intermediate Similarity	NPC211135
0.8444	Intermediate Similarity	NPC216420
0.8444	Intermediate Similarity	NPC207013
0.8444	Intermediate Similarity	NPC85095
0.8438	Intermediate Similarity	NPC279974
0.8438	Intermediate Similarity	NPC8774
0.8416	Intermediate Similarity	NPC473199
0.8404	Intermediate Similarity	NPC11216
0.8404	Intermediate Similarity	NPC291484
0.8404	Intermediate Similarity	NPC204188
0.8404	Intermediate Similarity	NPC329596
0.8404	Intermediate Similarity	NPC3345
0.8404	Intermediate Similarity	NPC80561
0.84	Intermediate Similarity	NPC473523
0.837	Intermediate Similarity	NPC121981
0.837	Intermediate Similarity	NPC201273
0.837	Intermediate Similarity	NPC71520
0.837	Intermediate Similarity	NPC269058
0.8367	Intermediate Similarity	NPC476895
0.8352	Intermediate Similarity	NPC475798
0.8352	Intermediate Similarity	NPC127606
0.8352	Intermediate Similarity	NPC299963
0.8351	Intermediate Similarity	NPC292718
0.8351	Intermediate Similarity	NPC111834
0.8351	Intermediate Similarity	NPC227583
0.8351	Intermediate Similarity	NPC306797
0.8351	Intermediate Similarity	NPC12103
0.8351	Intermediate Similarity	NPC288970
0.8351	Intermediate Similarity	NPC169270
0.8351	Intermediate Similarity	NPC98457
0.835	Intermediate Similarity	NPC154085
0.835	Intermediate Similarity	NPC43976
0.835	Intermediate Similarity	NPC125361
0.835	Intermediate Similarity	NPC296761
0.835	Intermediate Similarity	NPC51925
0.8333	Intermediate Similarity	NPC59530
0.8333	Intermediate Similarity	NPC127718
0.8333	Intermediate Similarity	NPC65402
0.8317	Intermediate Similarity	NPC470064
0.8317	Intermediate Similarity	NPC470062
0.8317	Intermediate Similarity	NPC31430
0.8317	Intermediate Similarity	NPC470058
0.8317	Intermediate Similarity	NPC470057
0.8317	Intermediate Similarity	NPC470043
0.8317	Intermediate Similarity	NPC470059
0.8317	Intermediate Similarity	NPC85593
0.8317	Intermediate Similarity	NPC470061
0.8317	Intermediate Similarity	NPC470060
0.8316	Intermediate Similarity	NPC210268
0.83	Intermediate Similarity	NPC154452
0.8298	Intermediate Similarity	NPC105495
0.8298	Intermediate Similarity	NPC470361
0.8283	Intermediate Similarity	NPC476195
0.8283	Intermediate Similarity	NPC254567
0.8283	Intermediate Similarity	NPC474571
0.8283	Intermediate Similarity	NPC38855
0.8265	Intermediate Similarity	NPC274793
0.8265	Intermediate Similarity	NPC477226
0.8265	Intermediate Similarity	NPC278939
0.8265	Intermediate Similarity	NPC473555
0.8265	Intermediate Similarity	NPC471770
0.8261	Intermediate Similarity	NPC266651
0.8261	Intermediate Similarity	NPC164424
0.8252	Intermediate Similarity	NPC472988
0.8252	Intermediate Similarity	NPC38217
0.8247	Intermediate Similarity	NPC276110
0.8247	Intermediate Similarity	NPC241047
0.8242	Intermediate Similarity	NPC193870
0.8242	Intermediate Similarity	NPC141941
0.8235	Intermediate Similarity	NPC220217
0.8235	Intermediate Similarity	NPC119855
0.8235	Intermediate Similarity	NPC186668
0.8229	Intermediate Similarity	NPC26046
0.8218	Intermediate Similarity	NPC10232
0.8218	Intermediate Similarity	NPC472821
0.8218	Intermediate Similarity	NPC196471
0.8218	Intermediate Similarity	NPC187302
0.8218	Intermediate Similarity	NPC189588
0.8218	Intermediate Similarity	NPC97487
0.8218	Intermediate Similarity	NPC474575
0.8211	Intermediate Similarity	NPC123252
0.8211	Intermediate Similarity	NPC219937
0.8211	Intermediate Similarity	NPC194485
0.8211	Intermediate Similarity	NPC53890
0.82	Intermediate Similarity	NPC476132
0.82	Intermediate Similarity	NPC96784
0.82	Intermediate Similarity	NPC21064
0.82	Intermediate Similarity	NPC256247
0.82	Intermediate Similarity	NPC476896
0.82	Intermediate Similarity	NPC121072
0.82	Intermediate Similarity	NPC235920
0.82	Intermediate Similarity	NPC49532
0.8191	Intermediate Similarity	NPC473436
0.8191	Intermediate Similarity	NPC160304
0.8191	Intermediate Similarity	NPC133588
0.8191	Intermediate Similarity	NPC474668
0.819	Intermediate Similarity	NPC65167
0.819	Intermediate Similarity	NPC470076
0.8182	Intermediate Similarity	NPC157739
0.8182	Intermediate Similarity	NPC477854
0.8172	Intermediate Similarity	NPC94462
0.8172	Intermediate Similarity	NPC299068
0.8163	Intermediate Similarity	NPC475178
0.8163	Intermediate Similarity	NPC210717
0.8163	Intermediate Similarity	NPC103165
0.8163	Intermediate Similarity	NPC276103
0.8163	Intermediate Similarity	NPC54248
0.8163	Intermediate Similarity	NPC299654
0.8155	Intermediate Similarity	NPC234160
0.8152	Intermediate Similarity	NPC255882
0.8144	Intermediate Similarity	NPC3359
0.8144	Intermediate Similarity	NPC277399
0.8144	Intermediate Similarity	NPC474922
0.8137	Intermediate Similarity	NPC471293
0.8132	Intermediate Similarity	NPC472504
0.8132	Intermediate Similarity	NPC30166
0.8125	Intermediate Similarity	NPC130840
0.8125	Intermediate Similarity	NPC234335
0.8125	Intermediate Similarity	NPC189520
0.8119	Intermediate Similarity	NPC136816
0.8113	Intermediate Similarity	NPC44537
0.8111	Intermediate Similarity	NPC206735
0.8111	Intermediate Similarity	NPC236237
0.8111	Intermediate Similarity	NPC13554
0.8111	Intermediate Similarity	NPC322313
0.8111	Intermediate Similarity	NPC102253
0.81	Intermediate Similarity	NPC477655
0.81	Intermediate Similarity	NPC167974
0.8095	Intermediate Similarity	NPC177047
0.8095	Intermediate Similarity	NPC472214
0.8095	Intermediate Similarity	NPC472215
0.8081	Intermediate Similarity	NPC261807
0.8065	Intermediate Similarity	NPC470360
0.8061	Intermediate Similarity	NPC476894
0.8058	Intermediate Similarity	NPC470055
0.8058	Intermediate Similarity	NPC477877
0.8058	Intermediate Similarity	NPC472655
0.8058	Intermediate Similarity	NPC470056
0.8043	Intermediate Similarity	NPC110778
0.8043	Intermediate Similarity	NPC113978

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 NPC471903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1515
0.2-0.3	4061
0.3-0.4	2308
0.4-0.5	619
0.5-0.6	205
0.6-0.7	196
0.7-0.8	88
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8111	Intermediate Similarity	NPD7525	Registered
0.7895	Intermediate Similarity	NPD7524	Approved
0.7838	Intermediate Similarity	NPD7516	Approved
0.7822	Intermediate Similarity	NPD7638	Approved
0.7766	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7327	Approved
0.7748	Intermediate Similarity	NPD7328	Approved
0.7745	Intermediate Similarity	NPD7640	Approved
0.7745	Intermediate Similarity	NPD7639	Approved
0.7677	Intermediate Similarity	NPD6399	Phase 3
0.766	Intermediate Similarity	NPD6695	Phase 3
0.7576	Intermediate Similarity	NPD7637	Suspended
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.7544	Intermediate Similarity	NPD8296	Approved
0.7544	Intermediate Similarity	NPD8033	Approved
0.7544	Intermediate Similarity	NPD8380	Approved
0.7544	Intermediate Similarity	NPD8335	Approved
0.7544	Intermediate Similarity	NPD8379	Approved
0.7544	Intermediate Similarity	NPD8378	Approved
0.7477	Intermediate Similarity	NPD5697	Approved
0.7456	Intermediate Similarity	NPD8294	Approved
0.7456	Intermediate Similarity	NPD8377	Approved
0.7455	Intermediate Similarity	NPD8297	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD8034	Phase 2
0.7391	Intermediate Similarity	NPD6932	Approved
0.7387	Intermediate Similarity	NPD4632	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7363	Intermediate Similarity	NPD6942	Approved
0.7363	Intermediate Similarity	NPD7339	Approved
0.7347	Intermediate Similarity	NPD7750	Discontinued
0.7345	Intermediate Similarity	NPD7115	Discovery
0.734	Intermediate Similarity	NPD6930	Phase 2
0.734	Intermediate Similarity	NPD6931	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5701	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.7283	Intermediate Similarity	NPD6933	Approved
0.7248	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6011	Approved
0.7241	Intermediate Similarity	NPD7503	Approved
0.7234	Intermediate Similarity	NPD7645	Phase 2
0.7234	Intermediate Similarity	NPD6929	Approved
0.7216	Intermediate Similarity	NPD4786	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7191	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7514	Phase 3
0.7143	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.7128	Intermediate Similarity	NPD6697	Approved
0.7128	Intermediate Similarity	NPD7145	Approved
0.7128	Intermediate Similarity	NPD6114	Approved
0.7128	Intermediate Similarity	NPD6118	Approved
0.7128	Intermediate Similarity	NPD6115	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.7107	Intermediate Similarity	NPD7319	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7748	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7065	Intermediate Similarity	NPD6926	Approved
0.7065	Intermediate Similarity	NPD6924	Approved
0.7064	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD7087	Discontinued
0.7059	Intermediate Similarity	NPD6079	Approved
0.7059	Intermediate Similarity	NPD7492	Approved
0.7059	Intermediate Similarity	NPD7515	Phase 2
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6683	Phase 2
0.7048	Intermediate Similarity	NPD4755	Approved
0.7048	Intermediate Similarity	NPD7902	Approved
0.7043	Intermediate Similarity	NPD6009	Approved
0.703	Intermediate Similarity	NPD6051	Approved
0.703	Intermediate Similarity	NPD5328	Approved
0.7025	Intermediate Similarity	NPD7736	Approved
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.7021	Intermediate Similarity	NPD6925	Approved
0.7021	Intermediate Similarity	NPD5776	Phase 2
0.701	Intermediate Similarity	NPD3667	Approved
0.7009	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6616	Approved
0.699	Remote Similarity	NPD4202	Approved
0.6979	Remote Similarity	NPD7332	Phase 2
0.6975	Remote Similarity	NPD7604	Phase 2
0.697	Remote Similarity	NPD6893	Approved
0.6949	Remote Similarity	NPD5983	Phase 2
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD5224	Approved
0.6942	Remote Similarity	NPD7078	Approved
0.693	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6916	Remote Similarity	NPD4700	Approved
0.6916	Remote Similarity	NPD6648	Approved
0.6915	Remote Similarity	NPD6117	Approved
0.6907	Remote Similarity	NPD6902	Approved
0.69	Remote Similarity	NPD3618	Phase 1
0.6891	Remote Similarity	NPD6370	Approved
0.6882	Remote Similarity	NPD4784	Approved
0.6882	Remote Similarity	NPD4785	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6875	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6059	Approved
0.686	Remote Similarity	NPD6336	Discontinued
0.6857	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD5223	Approved
0.6848	Remote Similarity	NPD7152	Approved
0.6848	Remote Similarity	NPD7150	Approved
0.6848	Remote Similarity	NPD7151	Approved
0.6838	Remote Similarity	NPD6335	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6274	Approved
0.6807	Remote Similarity	NPD6016	Approved
0.6807	Remote Similarity	NPD6015	Approved
0.6804	Remote Similarity	NPD7509	Discontinued
0.6803	Remote Similarity	NPD8293	Discontinued
0.6792	Remote Similarity	NPD5221	Approved
0.6792	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5222	Approved
0.6786	Remote Similarity	NPD6686	Approved
0.6765	Remote Similarity	NPD6672	Approved
0.6765	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5737	Approved
0.6762	Remote Similarity	NPD7900	Approved
0.6762	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6317	Approved
0.675	Remote Similarity	NPD5988	Approved
0.6739	Remote Similarity	NPD7144	Approved
0.6739	Remote Similarity	NPD7143	Approved
0.6735	Remote Similarity	NPD6898	Phase 1
0.6733	Remote Similarity	NPD6409	Approved
0.6733	Remote Similarity	NPD5330	Approved
0.6733	Remote Similarity	NPD7521	Approved
0.6733	Remote Similarity	NPD6684	Approved
0.6733	Remote Similarity	NPD7334	Approved
0.6733	Remote Similarity	NPD7146	Approved
0.6731	Remote Similarity	NPD6411	Approved
0.6729	Remote Similarity	NPD5173	Approved
0.6702	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4195	Approved
0.6699	Remote Similarity	NPD4753	Phase 2
0.6698	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4159	Approved
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4697	Phase 3
0.6633	Remote Similarity	NPD4748	Discontinued
0.6633	Remote Similarity	NPD4820	Approved
0.6633	Remote Similarity	NPD4819	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4821	Approved
0.6633	Remote Similarity	NPD4822	Approved
0.663	Remote Similarity	NPD6923	Approved
0.663	Remote Similarity	NPD6922	Approved
0.661	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4768	Approved
0.6607	Remote Similarity	NPD4767	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6577	Remote Similarity	NPD4754	Approved
0.6571	Remote Similarity	NPD5281	Approved
0.6571	Remote Similarity	NPD5284	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