NPASS Compound

Structure

NPC472928 OpenBabel07101718192D 38 41 0 0 1 0 0 0 0 0999 V2000 -0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 5.3212 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 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 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 -2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 -1.5388 0.5000 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 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 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 1.7321 0.0000 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 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5180 5.8564 0.0000 C 0 0 0 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 3.4641 -2.0000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 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 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8270 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 5.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 16 1 0 0 0 0 5 29 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 27 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 28 1 0 0 0 0 14 31 1 0 0 0 0 15 1 1 1 0 0 0 15 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 6 0 0 0 18 22 1 0 0 0 0 18 32 1 6 0 0 0 19 27 1 6 0 0 0 19 28 1 0 0 0 0 20 28 1 0 0 0 0 20 33 2 0 0 0 0 21 30 1 0 0 0 0 21 34 2 0 0 0 0 22 23 2 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 35 2 0 0 0 0 25 29 1 1 0 0 0 25 36 1 0 0 0 0 26 37 2 0 0 0 0 26 38 1 0 0 0 0 27 3 1 6 0 0 0 28 4 1 6 0 0 0 29 30 1 6 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.29
Volume:	547.713
LogP:	2.331
LogD:	1.076
LogS:	-2.777
# Rotatable Bonds:	6
TPSA:	146.04
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	5.422
Fsp3:	0.767
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:	-5.378
MDCK Permeability:	1.5202342183329165e-05
Pgp-inhibitor:	0.591
Pgp-substrate:	0.127
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.499
Plasma Protein Binding (PPB):	70.9770736694336%
Volume Distribution (VD):	0.429
Pgp-substrate:	17.124399185180664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.432
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.719
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.137
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.093
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	3.774
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.319
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.67
Skin Sensitization:	0.121
Carcinogencity:	0.03
Eye Corrosion:	0.033
Eye Irritation:	0.021
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC472928

Natural Product ID:	NPC472928
*Common Name:**	ASVBQOYWONHOKP-XQJOPQQLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ASVBQOYWONHOKP-XQJOPQQLSA-N
Standard InCHI:	InChI=1S/C30H42O8/c1-15(8-7-9-16(2)26(37)38)17-12-21(34)30(6)22-18(32)13-19-27(3,11-10-20(33)28(19,4)14-31)23(22)24(35)25(36)29(17,30)5/h9,15,17-19,25,31-32,36H,7-8,10-14H2,1-6H3,(H,37,38)/b16-9+/t15-,17-,18+,19-,25+,27+,28+,29+,30+/m1/s1
SMILES:	CC(CCC=C(C)C(=O)O)C1CC(=O)C2(C1(C(C(=O)C3=C2C(CC4C3(CCC(=O)C4(C)CO)C)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594146
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33020	ganoderma leucocontextum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Tibetan	n.a.	PMID[26287401]

☑ 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	4

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1088	Individual Protein	3-hydroxy-3-methylglutaryl-coenzyme A reductase	Sus scrofa	IC50	>	100000.0	nM	PMID[527438]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	200000.0	nM	PMID[527438]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	200000.0	nM	PMID[527438]
NPT2	Others	Unspecified		IC50	=	12700.0	nM	PMID[527438]

☑ 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 NPC472928 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	199
0.1-0.2	1212
0.2-0.3	4721
0.3-0.4	8912
0.4-0.5	12699
0.5-0.6	7179
0.6-0.7	5763
0.7-0.8	1815
0.8-0.85	129
0.85-0.9	55
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9608	High Similarity	NPC472925
0.9533	High Similarity	NPC472927
0.9515	High Similarity	NPC295244
0.9358	High Similarity	NPC472933
0.932	High Similarity	NPC51452
0.9314	High Similarity	NPC251017
0.9252	High Similarity	NPC472926
0.9252	High Similarity	NPC472929
0.9216	High Similarity	NPC293753
0.9174	High Similarity	NPC472934
0.9118	High Similarity	NPC472924
0.9057	High Similarity	NPC286174
0.9057	High Similarity	NPC77947
0.9029	High Similarity	NPC234892
0.902	High Similarity	NPC327431
0.902	High Similarity	NPC287833
0.8972	High Similarity	NPC129689
0.8889	High Similarity	NPC115303
0.8835	High Similarity	NPC51370
0.8835	High Similarity	NPC157787
0.8824	High Similarity	NPC122294
0.8824	High Similarity	NPC43747
0.8824	High Similarity	NPC320306
0.8796	High Similarity	NPC272898
0.8796	High Similarity	NPC473036
0.875	High Similarity	NPC163372
0.875	High Similarity	NPC302537
0.8738	High Similarity	NPC16021
0.8725	High Similarity	NPC96859
0.8725	High Similarity	NPC472941
0.8725	High Similarity	NPC456
0.8725	High Similarity	NPC305483
0.8725	High Similarity	NPC328162
0.8667	High Similarity	NPC308726
0.8667	High Similarity	NPC119601
0.8654	High Similarity	NPC299971
0.8654	High Similarity	NPC307954
0.8654	High Similarity	NPC88198
0.8654	High Similarity	NPC144660
0.8627	High Similarity	NPC469995
0.8627	High Similarity	NPC173875
0.8627	High Similarity	NPC174948
0.8627	High Similarity	NPC318282
0.8627	High Similarity	NPC37646
0.8598	High Similarity	NPC323834
0.8585	High Similarity	NPC55872
0.8585	High Similarity	NPC33973
0.8585	High Similarity	NPC70967
0.8558	High Similarity	NPC114274
0.8558	High Similarity	NPC197386
0.8544	High Similarity	NPC3772
0.8544	High Similarity	NPC40765
0.8544	High Similarity	NPC328371
0.8544	High Similarity	NPC243525
0.8529	High Similarity	NPC166906
0.8519	High Similarity	NPC473037
0.8519	High Similarity	NPC185
0.8505	High Similarity	NPC470251
0.8505	High Similarity	NPC216245
0.8505	High Similarity	NPC2436
0.8505	High Similarity	NPC96268
0.8505	High Similarity	NPC135854
0.8505	High Similarity	NPC28656
0.8496	Intermediate Similarity	NPC239273
0.8491	Intermediate Similarity	NPC136289
0.8491	Intermediate Similarity	NPC281702
0.8491	Intermediate Similarity	NPC204450
0.8491	Intermediate Similarity	NPC195290
0.8476	Intermediate Similarity	NPC476274
0.8468	Intermediate Similarity	NPC264634
0.8462	Intermediate Similarity	NPC106557
0.8462	Intermediate Similarity	NPC108078
0.8462	Intermediate Similarity	NPC121339
0.8447	Intermediate Similarity	NPC255809
0.8447	Intermediate Similarity	NPC470016
0.8447	Intermediate Similarity	NPC297199
0.8447	Intermediate Similarity	NPC317586
0.8435	Intermediate Similarity	NPC109973
0.8431	Intermediate Similarity	NPC69454
0.8411	Intermediate Similarity	NPC159442
0.8411	Intermediate Similarity	NPC249187
0.8411	Intermediate Similarity	NPC247957
0.8411	Intermediate Similarity	NPC236390
0.8407	Intermediate Similarity	NPC148458
0.8396	Intermediate Similarity	NPC476240
0.8396	Intermediate Similarity	NPC124211
0.8396	Intermediate Similarity	NPC81530
0.8396	Intermediate Similarity	NPC476223
0.8396	Intermediate Similarity	NPC224720
0.8381	Intermediate Similarity	NPC471717
0.8381	Intermediate Similarity	NPC147954
0.8365	Intermediate Similarity	NPC7124
0.8365	Intermediate Similarity	NPC249954
0.8365	Intermediate Similarity	NPC173272
0.835	Intermediate Similarity	NPC245972
0.835	Intermediate Similarity	NPC196485
0.8333	Intermediate Similarity	NPC63748
0.8333	Intermediate Similarity	NPC233116
0.8333	Intermediate Similarity	NPC72255
0.8333	Intermediate Similarity	NPC471854
0.8318	Intermediate Similarity	NPC473424
0.8318	Intermediate Similarity	NPC53222
0.8304	Intermediate Similarity	NPC71348
0.8304	Intermediate Similarity	NPC147180
0.8302	Intermediate Similarity	NPC316964
0.8302	Intermediate Similarity	NPC198880
0.8288	Intermediate Similarity	NPC286880
0.8273	Intermediate Similarity	NPC65941
0.8269	Intermediate Similarity	NPC48330
0.8269	Intermediate Similarity	NPC259286
0.8269	Intermediate Similarity	NPC271195
0.8261	Intermediate Similarity	NPC21326
0.8257	Intermediate Similarity	NPC472935
0.8257	Intermediate Similarity	NPC166607
0.8257	Intermediate Similarity	NPC257353
0.8257	Intermediate Similarity	NPC149047
0.8252	Intermediate Similarity	NPC472930
0.8246	Intermediate Similarity	NPC270958
0.8241	Intermediate Similarity	NPC312900
0.8241	Intermediate Similarity	NPC95899
0.8241	Intermediate Similarity	NPC111323
0.8241	Intermediate Similarity	NPC275583
0.8241	Intermediate Similarity	NPC311612
0.823	Intermediate Similarity	NPC202889
0.823	Intermediate Similarity	NPC962
0.823	Intermediate Similarity	NPC73300
0.823	Intermediate Similarity	NPC250109
0.823	Intermediate Similarity	NPC108721
0.8208	Intermediate Similarity	NPC10364
0.8208	Intermediate Similarity	NPC235464
0.8208	Intermediate Similarity	NPC103051
0.8208	Intermediate Similarity	NPC478056
0.8208	Intermediate Similarity	NPC166745
0.8198	Intermediate Similarity	NPC304495
0.8198	Intermediate Similarity	NPC214644
0.8198	Intermediate Similarity	NPC11710
0.819	Intermediate Similarity	NPC117133
0.819	Intermediate Similarity	NPC95565
0.8182	Intermediate Similarity	NPC220229
0.8182	Intermediate Similarity	NPC91034
0.8182	Intermediate Similarity	NPC58370
0.8182	Intermediate Similarity	NPC165873
0.8182	Intermediate Similarity	NPC43285
0.8182	Intermediate Similarity	NPC475060
0.8182	Intermediate Similarity	NPC475294
0.8173	Intermediate Similarity	NPC469406
0.8173	Intermediate Similarity	NPC119562
0.8173	Intermediate Similarity	NPC279410
0.8173	Intermediate Similarity	NPC184870
0.8167	Intermediate Similarity	NPC470882
0.8167	Intermediate Similarity	NPC473265
0.8165	Intermediate Similarity	NPC160843
0.8165	Intermediate Similarity	NPC209502
0.8165	Intermediate Similarity	NPC204833
0.8158	Intermediate Similarity	NPC470953
0.8155	Intermediate Similarity	NPC168027
0.8155	Intermediate Similarity	NPC185936
0.8155	Intermediate Similarity	NPC107690
0.8148	Intermediate Similarity	NPC473788
0.8148	Intermediate Similarity	NPC87351
0.8148	Intermediate Similarity	NPC475558
0.8142	Intermediate Similarity	NPC475524
0.8142	Intermediate Similarity	NPC221144
0.8142	Intermediate Similarity	NPC100267
0.8137	Intermediate Similarity	NPC275740
0.8137	Intermediate Similarity	NPC214387
0.8137	Intermediate Similarity	NPC86319
0.8136	Intermediate Similarity	NPC269642
0.8136	Intermediate Similarity	NPC222688
0.8131	Intermediate Similarity	NPC474720
0.8131	Intermediate Similarity	NPC154072
0.8131	Intermediate Similarity	NPC205899
0.813	Intermediate Similarity	NPC469674
0.8125	Intermediate Similarity	NPC197428
0.812	Intermediate Similarity	NPC476962
0.8113	Intermediate Similarity	NPC273269
0.8113	Intermediate Similarity	NPC253826
0.8113	Intermediate Similarity	NPC18319
0.8113	Intermediate Similarity	NPC216904
0.8108	Intermediate Similarity	NPC217201
0.8103	Intermediate Similarity	NPC311554
0.8103	Intermediate Similarity	NPC118638
0.8103	Intermediate Similarity	NPC257457
0.8095	Intermediate Similarity	NPC472932
0.8095	Intermediate Similarity	NPC241156
0.8091	Intermediate Similarity	NPC50692
0.8091	Intermediate Similarity	NPC260268
0.8091	Intermediate Similarity	NPC150531
0.8091	Intermediate Similarity	NPC48733
0.8091	Intermediate Similarity	NPC476027
0.8091	Intermediate Similarity	NPC171137
0.8091	Intermediate Similarity	NPC319077
0.8091	Intermediate Similarity	NPC296945
0.8091	Intermediate Similarity	NPC152695
0.8091	Intermediate Similarity	NPC49958
0.8091	Intermediate Similarity	NPC302607
0.8091	Intermediate Similarity	NPC202167
0.8091	Intermediate Similarity	NPC85829
0.8091	Intermediate Similarity	NPC214264
0.8091	Intermediate Similarity	NPC97202

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 NPC472928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1571
0.2-0.3	3794
0.3-0.4	2373
0.4-0.5	750
0.5-0.6	209
0.6-0.7	180
0.7-0.8	103
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
0.8053	Intermediate Similarity	NPD6650	Approved
0.8053	Intermediate Similarity	NPD6649	Approved
0.8036	Intermediate Similarity	NPD6372	Approved
0.8036	Intermediate Similarity	NPD6373	Approved
0.8019	Intermediate Similarity	NPD4697	Phase 3
0.8019	Intermediate Similarity	NPD5221	Approved
0.8019	Intermediate Similarity	NPD5222	Approved
0.8019	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD5211	Phase 2
0.7981	Intermediate Similarity	NPD6079	Approved
0.7961	Intermediate Similarity	NPD5328	Approved
0.7946	Intermediate Similarity	NPD6881	Approved
0.7946	Intermediate Similarity	NPD6899	Approved
0.7944	Intermediate Similarity	NPD5173	Approved
0.7928	Intermediate Similarity	NPD5739	Approved
0.7928	Intermediate Similarity	NPD7128	Approved
0.7928	Intermediate Similarity	NPD6675	Approved
0.7928	Intermediate Similarity	NPD6402	Approved
0.7863	Intermediate Similarity	NPD7115	Discovery
0.7857	Intermediate Similarity	NPD5697	Approved
0.7838	Intermediate Similarity	NPD5141	Approved
0.7826	Intermediate Similarity	NPD8297	Approved
0.7826	Intermediate Similarity	NPD6882	Approved
0.7815	Intermediate Similarity	NPD6319	Approved
0.7807	Intermediate Similarity	NPD7290	Approved
0.7807	Intermediate Similarity	NPD4634	Approved
0.7807	Intermediate Similarity	NPD6883	Approved
0.7807	Intermediate Similarity	NPD7102	Approved
0.7798	Intermediate Similarity	NPD5285	Approved
0.7798	Intermediate Similarity	NPD4696	Approved
0.7798	Intermediate Similarity	NPD5286	Approved
0.7788	Intermediate Similarity	NPD7320	Approved
0.7788	Intermediate Similarity	NPD6011	Approved
0.7778	Intermediate Similarity	NPD4755	Approved
0.7759	Intermediate Similarity	NPD4632	Approved
0.7739	Intermediate Similarity	NPD6847	Approved
0.7739	Intermediate Similarity	NPD8130	Phase 1
0.7739	Intermediate Similarity	NPD6617	Approved
0.7739	Intermediate Similarity	NPD6869	Approved
0.7727	Intermediate Similarity	NPD5223	Approved
0.7719	Intermediate Similarity	NPD6012	Approved
0.7719	Intermediate Similarity	NPD6014	Approved
0.7719	Intermediate Similarity	NPD6013	Approved
0.7699	Intermediate Similarity	NPD5701	Approved
0.767	Intermediate Similarity	NPD3618	Phase 1
0.7658	Intermediate Similarity	NPD5225	Approved
0.7658	Intermediate Similarity	NPD4633	Approved
0.7658	Intermediate Similarity	NPD5226	Approved
0.7658	Intermediate Similarity	NPD5224	Approved
0.7636	Intermediate Similarity	NPD4700	Approved
0.7636	Intermediate Similarity	NPD7640	Approved
0.7636	Intermediate Similarity	NPD7639	Approved
0.7593	Intermediate Similarity	NPD4629	Approved
0.7593	Intermediate Similarity	NPD5210	Approved
0.7589	Intermediate Similarity	NPD5175	Approved
0.7589	Intermediate Similarity	NPD5174	Approved
0.7586	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6399	Phase 3
0.7563	Intermediate Similarity	NPD6009	Approved
0.7561	Intermediate Similarity	NPD7492	Approved
0.7545	Intermediate Similarity	NPD7638	Approved
0.7545	Intermediate Similarity	NPD5696	Approved
0.7521	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD5279	Phase 3
0.7479	Intermediate Similarity	NPD6868	Approved
0.7478	Intermediate Similarity	NPD4729	Approved
0.7478	Intermediate Similarity	NPD4730	Approved
0.7477	Intermediate Similarity	NPD7515	Phase 2
0.7476	Intermediate Similarity	NPD4786	Approved
0.7456	Intermediate Similarity	NPD4767	Approved
0.7456	Intermediate Similarity	NPD6008	Approved
0.7456	Intermediate Similarity	NPD4768	Approved
0.7455	Intermediate Similarity	NPD6083	Phase 2
0.7455	Intermediate Similarity	NPD6084	Phase 2
0.744	Intermediate Similarity	NPD7078	Approved
0.7434	Intermediate Similarity	NPD4754	Approved
0.7431	Intermediate Similarity	NPD5695	Phase 3
0.7407	Intermediate Similarity	NPD5779	Approved
0.7407	Intermediate Similarity	NPD5778	Approved
0.7398	Intermediate Similarity	NPD6370	Approved
0.7381	Intermediate Similarity	NPD7736	Approved
0.7377	Intermediate Similarity	NPD6059	Approved
0.7358	Intermediate Similarity	NPD6672	Approved
0.7358	Intermediate Similarity	NPD5737	Approved
0.7355	Intermediate Similarity	NPD6335	Approved
0.735	Intermediate Similarity	NPD5247	Approved
0.735	Intermediate Similarity	NPD5248	Approved
0.735	Intermediate Similarity	NPD5249	Phase 3
0.735	Intermediate Similarity	NPD5251	Approved
0.735	Intermediate Similarity	NPD5250	Approved
0.7344	Intermediate Similarity	NPD7260	Phase 2
0.7339	Intermediate Similarity	NPD7604	Phase 2
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6274	Approved
0.7328	Intermediate Similarity	NPD5128	Approved
0.7328	Intermediate Similarity	NPD5168	Approved
0.7317	Intermediate Similarity	NPD6016	Approved
0.7317	Intermediate Similarity	NPD5983	Phase 2
0.7317	Intermediate Similarity	NPD6015	Approved
0.7302	Intermediate Similarity	NPD8293	Discontinued
0.7295	Intermediate Similarity	NPD7100	Approved
0.7295	Intermediate Similarity	NPD7101	Approved
0.729	Intermediate Similarity	NPD4753	Phase 2
0.7282	Intermediate Similarity	NPD3667	Approved
0.7273	Intermediate Similarity	NPD6317	Approved
0.7258	Intermediate Similarity	NPD5988	Approved
0.7248	Intermediate Similarity	NPD4202	Approved
0.7238	Intermediate Similarity	NPD5363	Approved
0.7232	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD5785	Approved
0.7222	Intermediate Similarity	NPD6336	Discontinued
0.7213	Intermediate Similarity	NPD6314	Approved
0.7213	Intermediate Similarity	NPD6313	Approved
0.7203	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5135	Approved
0.7203	Intermediate Similarity	NPD5169	Approved
0.72	Intermediate Similarity	NPD8328	Phase 3
0.7182	Intermediate Similarity	NPD7748	Approved
0.7177	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5690	Phase 2
0.7156	Intermediate Similarity	NPD5281	Approved
0.7156	Intermediate Similarity	NPD6411	Approved
0.7156	Intermediate Similarity	NPD5284	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD5215	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD5217	Approved
0.7075	Intermediate Similarity	NPD5329	Approved
0.7075	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7319	Approved
0.7043	Intermediate Similarity	NPD7632	Discontinued
0.704	Intermediate Similarity	NPD6909	Approved
0.704	Intermediate Similarity	NPD6908	Approved
0.7023	Intermediate Similarity	NPD6845	Suspended
0.7009	Intermediate Similarity	NPD5786	Approved
0.7009	Intermediate Similarity	NPD5330	Approved
0.7009	Intermediate Similarity	NPD4694	Approved
0.7009	Intermediate Similarity	NPD5280	Approved
0.7009	Intermediate Similarity	NPD7521	Approved
0.7009	Intermediate Similarity	NPD6684	Approved
0.7009	Intermediate Similarity	NPD7146	Approved
0.7009	Intermediate Similarity	NPD7334	Approved
0.7009	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD6050	Approved
0.6981	Remote Similarity	NPD4197	Approved
0.6977	Remote Similarity	NPD6033	Approved
0.6972	Remote Similarity	NPD6904	Approved
0.6972	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6673	Approved
0.6972	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6080	Approved
0.6972	Remote Similarity	NPD6101	Approved
0.6967	Remote Similarity	NPD5167	Approved
0.6964	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7507	Approved
0.6952	Remote Similarity	NPD4270	Approved
0.6952	Remote Similarity	NPD4269	Approved
0.6942	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD4695	Discontinued
0.6909	Remote Similarity	NPD5692	Phase 3
0.6893	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6903	Approved
0.6881	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6404	Discontinued
0.6855	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5693	Phase 1
0.6847	Remote Similarity	NPD8035	Phase 2
0.6847	Remote Similarity	NPD5694	Approved
0.6847	Remote Similarity	NPD8034	Phase 2
0.6822	Remote Similarity	NPD3668	Phase 3
0.6792	Remote Similarity	NPD4221	Approved
0.6792	Remote Similarity	NPD4223	Phase 3
0.6789	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD6333	Approved
0.6765	Remote Similarity	NPD6334	Approved
0.6762	Remote Similarity	NPD4252	Approved
0.6759	Remote Similarity	NPD1694	Approved
0.6759	Remote Similarity	NPD1696	Phase 3
0.6754	Remote Similarity	NPD7614	Phase 1
0.6752	Remote Similarity	NPD5091	Approved
0.675	Remote Similarity	NPD6686	Approved
0.6731	Remote Similarity	NPD6697	Approved
0.6731	Remote Similarity	NPD6114	Approved
0.6731	Remote Similarity	NPD3617	Approved
0.6731	Remote Similarity	NPD6115	Approved
0.6731	Remote Similarity	NPD6118	Approved
0.6697	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6371	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