NPASS Compound

Structure

NPC472940 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.2382 2.4680 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 2.9641 -2.8660 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 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 0.3872 2.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 3.5385 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 1.0000 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 0.8660 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3435 2.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7036 4.0737 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 2.0345 3.3305 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 1.7321 -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 2.5981 -1.5000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6744 1.6363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6818 3.8658 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 2 27 1 0 0 0 0 3 27 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 19 1 0 0 0 0 9 20 2 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 23 1 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 20 1 0 0 0 0 18 32 1 0 0 0 0 19 1 1 6 0 0 0 19 21 1 0 0 0 0 21 29 1 6 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 33 2 0 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 34 2 0 0 0 0 26 30 1 0 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:	470.34
Volume:	517.825
LogP:	4.515
LogD:	4.134
LogS:	-4.817
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	4.861
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.064
MDCK Permeability:	1.6091635188786313e-05
Pgp-inhibitor:	0.643
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.915
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	90.2541275024414%
Volume Distribution (VD):	0.879
Pgp-substrate:	1.6622331142425537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.469
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.372
CYP2C9-substrate:	0.181
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.818
CYP3A4-substrate:	0.802

ADMET: Excretion

Clearance (CL):	5.273
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.666
Skin Sensitization:	0.174
Carcinogencity:	0.159
Eye Corrosion:	0.005
Eye Irritation:	0.136
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC472940

Natural Product ID:	NPC472940
*Common Name:**	HZCCGGOBXSVZRJ-XRLJWPMHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HZCCGGOBXSVZRJ-XRLJWPMHSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-19(8-7-9-20(17-31)18-32)21-10-15-30(6)26-22(11-14-29(21,30)5)28(4)13-12-25(34)27(2,3)24(28)16-23(26)33/h9,19,21,24,31-32H,7-8,10-18H2,1-6H3/t19-,21-,24+,28-,29-,30+/m1/s1
SMILES:	OCC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594158
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	=	12600.0	nM	PMID[536668]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	41600.0	nM	PMID[536668]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	200000.0	nM	PMID[536668]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[536668]

☑ 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 NPC472940 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	138
0.1-0.2	1160
0.2-0.3	6434
0.3-0.4	15683
0.4-0.5	8308
0.5-0.6	6950
0.6-0.7	3178
0.7-0.8	758
0.8-0.85	69
0.85-0.9	12
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472931
0.9747	High Similarity	NPC41539
0.9136	High Similarity	NPC311092
0.9036	High Similarity	NPC8571
0.9012	High Similarity	NPC4166
0.875	High Similarity	NPC472930
0.8675	High Similarity	NPC142253
0.8675	High Similarity	NPC3511
0.8667	High Similarity	NPC472941
0.8667	High Similarity	NPC456
0.8588	High Similarity	NPC474083
0.8556	High Similarity	NPC472932
0.8537	High Similarity	NPC90965
0.8471	Intermediate Similarity	NPC473246
0.8471	Intermediate Similarity	NPC87552
0.8452	Intermediate Similarity	NPC472239
0.8427	Intermediate Similarity	NPC473998
0.8427	Intermediate Similarity	NPC23217
0.8415	Intermediate Similarity	NPC82635
0.8409	Intermediate Similarity	NPC309603
0.8409	Intermediate Similarity	NPC473999
0.8387	Intermediate Similarity	NPC51370
0.8387	Intermediate Similarity	NPC287833
0.8372	Intermediate Similarity	NPC11711
0.8372	Intermediate Similarity	NPC471224
0.8354	Intermediate Similarity	NPC223187
0.8333	Intermediate Similarity	NPC472942
0.8333	Intermediate Similarity	NPC69454
0.8315	Intermediate Similarity	NPC48010
0.8276	Intermediate Similarity	NPC118648
0.8276	Intermediate Similarity	NPC475022
0.8276	Intermediate Similarity	NPC222613
0.8261	Intermediate Similarity	NPC249954
0.8256	Intermediate Similarity	NPC214043
0.8256	Intermediate Similarity	NPC85774
0.8242	Intermediate Similarity	NPC8993
0.8235	Intermediate Similarity	NPC472867
0.8222	Intermediate Similarity	NPC233116
0.8222	Intermediate Similarity	NPC63748
0.8222	Intermediate Similarity	NPC475806
0.8211	Intermediate Similarity	NPC293753
0.8211	Intermediate Similarity	NPC234892
0.8202	Intermediate Similarity	NPC31985
0.8202	Intermediate Similarity	NPC123912
0.8202	Intermediate Similarity	NPC1015
0.8202	Intermediate Similarity	NPC214387
0.8182	Intermediate Similarity	NPC99909
0.8161	Intermediate Similarity	NPC469948
0.8161	Intermediate Similarity	NPC123319
0.8161	Intermediate Similarity	NPC94531
0.8161	Intermediate Similarity	NPC311702
0.8161	Intermediate Similarity	NPC60350
0.8152	Intermediate Similarity	NPC318282
0.8152	Intermediate Similarity	NPC297199
0.8152	Intermediate Similarity	NPC37646
0.8152	Intermediate Similarity	NPC469995
0.8152	Intermediate Similarity	NPC259286
0.8152	Intermediate Similarity	NPC174948
0.8152	Intermediate Similarity	NPC173875
0.8132	Intermediate Similarity	NPC233118
0.8132	Intermediate Similarity	NPC474736
0.8111	Intermediate Similarity	NPC69622
0.8111	Intermediate Similarity	NPC477149
0.8111	Intermediate Similarity	NPC477147
0.8095	Intermediate Similarity	NPC472490
0.8095	Intermediate Similarity	NPC170793
0.809	Intermediate Similarity	NPC471722
0.8085	Intermediate Similarity	NPC197386
0.8085	Intermediate Similarity	NPC235464
0.8085	Intermediate Similarity	NPC166745
0.8072	Intermediate Similarity	NPC91665
0.8068	Intermediate Similarity	NPC469994
0.8068	Intermediate Similarity	NPC474778
0.8068	Intermediate Similarity	NPC72133
0.8068	Intermediate Similarity	NPC145879
0.8068	Intermediate Similarity	NPC474733
0.8068	Intermediate Similarity	NPC474732
0.8068	Intermediate Similarity	NPC31564
0.8065	Intermediate Similarity	NPC3772
0.8065	Intermediate Similarity	NPC243525
0.8065	Intermediate Similarity	NPC40765
0.8065	Intermediate Similarity	NPC328371
0.8046	Intermediate Similarity	NPC237712
0.8046	Intermediate Similarity	NPC178025
0.8046	Intermediate Similarity	NPC16287
0.8046	Intermediate Similarity	NPC181743
0.8025	Intermediate Similarity	NPC470044
0.8025	Intermediate Similarity	NPC474228
0.8025	Intermediate Similarity	NPC303613
0.8025	Intermediate Similarity	NPC470045
0.8	Intermediate Similarity	NPC86319
0.8	Intermediate Similarity	NPC159577
0.8	Intermediate Similarity	NPC477943
0.8	Intermediate Similarity	NPC2983
0.8	Intermediate Similarity	NPC275740
0.8	Intermediate Similarity	NPC282593
0.8	Intermediate Similarity	NPC472478
0.8	Intermediate Similarity	NPC310010
0.8	Intermediate Similarity	NPC35734
0.8	Intermediate Similarity	NPC326627
0.8	Intermediate Similarity	NPC307176
0.7979	Intermediate Similarity	NPC156546
0.7979	Intermediate Similarity	NPC320306
0.7979	Intermediate Similarity	NPC121339
0.7979	Intermediate Similarity	NPC122294
0.7979	Intermediate Similarity	NPC106557
0.7978	Intermediate Similarity	NPC58063
0.7978	Intermediate Similarity	NPC317590
0.7978	Intermediate Similarity	NPC90652
0.7978	Intermediate Similarity	NPC93778
0.7978	Intermediate Similarity	NPC136948
0.7978	Intermediate Similarity	NPC287079
0.7978	Intermediate Similarity	NPC475740
0.7978	Intermediate Similarity	NPC136548
0.7959	Intermediate Similarity	NPC472935
0.7957	Intermediate Similarity	NPC271195
0.7957	Intermediate Similarity	NPC476174
0.7938	Intermediate Similarity	NPC111323
0.7931	Intermediate Similarity	NPC279639
0.7931	Intermediate Similarity	NPC470015
0.7931	Intermediate Similarity	NPC168188
0.7931	Intermediate Similarity	NPC3856
0.7917	Intermediate Similarity	NPC472924
0.7912	Intermediate Similarity	NPC191684
0.7912	Intermediate Similarity	NPC320026
0.7912	Intermediate Similarity	NPC129913
0.7907	Intermediate Similarity	NPC116797
0.7901	Intermediate Similarity	NPC115023
0.7895	Intermediate Similarity	NPC16021
0.7895	Intermediate Similarity	NPC147954
0.7895	Intermediate Similarity	NPC471717
0.7889	Intermediate Similarity	NPC470417
0.7889	Intermediate Similarity	NPC131470
0.7889	Intermediate Similarity	NPC44181
0.7889	Intermediate Similarity	NPC143767
0.7879	Intermediate Similarity	NPC185
0.7875	Intermediate Similarity	NPC139397
0.7872	Intermediate Similarity	NPC29152
0.7872	Intermediate Similarity	NPC117133
0.7849	Intermediate Similarity	NPC469406
0.7849	Intermediate Similarity	NPC184870
0.7849	Intermediate Similarity	NPC318332
0.7849	Intermediate Similarity	NPC474690
0.7841	Intermediate Similarity	NPC164577
0.7841	Intermediate Similarity	NPC58841
0.7841	Intermediate Similarity	NPC230527
0.7841	Intermediate Similarity	NPC321187
0.7841	Intermediate Similarity	NPC82902
0.7841	Intermediate Similarity	NPC59453
0.7841	Intermediate Similarity	NPC476412
0.7841	Intermediate Similarity	NPC221758
0.7841	Intermediate Similarity	NPC320801
0.7841	Intermediate Similarity	NPC7927
0.7841	Intermediate Similarity	NPC161423
0.7841	Intermediate Similarity	NPC329043
0.7841	Intermediate Similarity	NPC227064
0.7841	Intermediate Similarity	NPC165064
0.7841	Intermediate Similarity	NPC209882
0.7835	Intermediate Similarity	NPC204450
0.7835	Intermediate Similarity	NPC87351
0.7835	Intermediate Similarity	NPC195290
0.7835	Intermediate Similarity	NPC473424
0.7831	Intermediate Similarity	NPC469803
0.7826	Intermediate Similarity	NPC19114
0.7826	Intermediate Similarity	NPC204341
0.7816	Intermediate Similarity	NPC469799
0.7816	Intermediate Similarity	NPC469805
0.7816	Intermediate Similarity	NPC469806
0.7816	Intermediate Similarity	NPC320514
0.7816	Intermediate Similarity	NPC469804
0.7812	Intermediate Similarity	NPC307954
0.7812	Intermediate Similarity	NPC299971
0.7812	Intermediate Similarity	NPC154072
0.7812	Intermediate Similarity	NPC327431
0.7812	Intermediate Similarity	NPC144660
0.7805	Intermediate Similarity	NPC180015
0.7805	Intermediate Similarity	NPC56747
0.7805	Intermediate Similarity	NPC109576
0.7805	Intermediate Similarity	NPC251705
0.7805	Intermediate Similarity	NPC130016
0.7802	Intermediate Similarity	NPC262043
0.7802	Intermediate Similarity	NPC186688
0.7802	Intermediate Similarity	NPC26959
0.7802	Intermediate Similarity	NPC268406
0.78	Intermediate Similarity	NPC295244
0.7791	Intermediate Similarity	NPC474509
0.7791	Intermediate Similarity	NPC2482
0.7789	Intermediate Similarity	NPC43747
0.7778	Intermediate Similarity	NPC260040
0.7778	Intermediate Similarity	NPC251929
0.7778	Intermediate Similarity	NPC2634
0.7778	Intermediate Similarity	NPC265782
0.7778	Intermediate Similarity	NPC476293
0.7778	Intermediate Similarity	NPC96496
0.7766	Intermediate Similarity	NPC180950
0.7765	Intermediate Similarity	NPC469996
0.7765	Intermediate Similarity	NPC470052
0.7755	Intermediate Similarity	NPC236390
0.7755	Intermediate Similarity	NPC249187
0.7755	Intermediate Similarity	NPC311612

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 NPC472940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1507
0.2-0.3	4608
0.3-0.4	2094
0.4-0.5	397
0.5-0.6	178
0.6-0.7	178
0.7-0.8	53
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
0.8148	Intermediate Similarity	NPD5733	Approved
0.8	Intermediate Similarity	NPD4753	Phase 2
0.8	Intermediate Similarity	NPD4747	Approved
0.7957	Intermediate Similarity	NPD5210	Approved
0.7957	Intermediate Similarity	NPD4629	Approved
0.7927	Intermediate Similarity	NPD4687	Approved
0.7901	Intermediate Similarity	NPD5276	Approved
0.7875	Intermediate Similarity	NPD4137	Phase 3
0.7865	Intermediate Similarity	NPD5279	Phase 3
0.7841	Intermediate Similarity	NPD3665	Phase 1
0.7841	Intermediate Similarity	NPD3133	Approved
0.7841	Intermediate Similarity	NPD4786	Approved
0.7841	Intermediate Similarity	NPD3666	Approved
0.7802	Intermediate Similarity	NPD5328	Approved
0.7778	Intermediate Similarity	NPD4691	Approved
0.7667	Intermediate Similarity	NPD3618	Phase 1
0.7634	Intermediate Similarity	NPD6079	Approved
0.7614	Intermediate Similarity	NPD3667	Approved
0.7614	Intermediate Similarity	NPD4221	Approved
0.7614	Intermediate Similarity	NPD4223	Phase 3
0.7604	Intermediate Similarity	NPD6083	Phase 2
0.7604	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD5695	Phase 3
0.7556	Intermediate Similarity	NPD5329	Approved
0.7526	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD4058	Approved
0.7475	Intermediate Similarity	NPD5211	Phase 2
0.7473	Intermediate Similarity	NPD5280	Approved
0.7473	Intermediate Similarity	NPD4694	Approved
0.7473	Intermediate Similarity	NPD5690	Phase 2
0.7444	Intermediate Similarity	NPD4197	Approved
0.7423	Intermediate Similarity	NPD4755	Approved
0.7368	Intermediate Similarity	NPD4202	Approved
0.7356	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5141	Approved
0.732	Intermediate Similarity	NPD5221	Approved
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD4697	Phase 3
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6672	Approved
0.7312	Intermediate Similarity	NPD5737	Approved
0.7283	Intermediate Similarity	NPD4138	Approved
0.7283	Intermediate Similarity	NPD4689	Approved
0.7283	Intermediate Similarity	NPD4690	Approved
0.7283	Intermediate Similarity	NPD5205	Approved
0.7283	Intermediate Similarity	NPD4623	Approved
0.7283	Intermediate Similarity	NPD4688	Approved
0.7283	Intermediate Similarity	NPD4519	Discontinued
0.7283	Intermediate Similarity	NPD4693	Phase 3
0.7273	Intermediate Similarity	NPD5286	Approved
0.7273	Intermediate Similarity	NPD4700	Approved
0.7273	Intermediate Similarity	NPD4696	Approved
0.7273	Intermediate Similarity	NPD5285	Approved
0.7263	Intermediate Similarity	NPD5281	Approved
0.7263	Intermediate Similarity	NPD5284	Approved
0.7245	Intermediate Similarity	NPD5173	Approved
0.7188	Intermediate Similarity	NPD6399	Phase 3
0.7159	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7129	Intermediate Similarity	NPD5226	Approved
0.7129	Intermediate Similarity	NPD4633	Approved
0.7129	Intermediate Similarity	NPD5224	Approved
0.7129	Intermediate Similarity	NPD5225	Approved
0.7097	Intermediate Similarity	NPD6684	Approved
0.7097	Intermediate Similarity	NPD5330	Approved
0.7097	Intermediate Similarity	NPD6409	Approved
0.7097	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7521	Approved
0.7097	Intermediate Similarity	NPD7334	Approved
0.7097	Intermediate Similarity	NPD7146	Approved
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7083	Intermediate Similarity	NPD7515	Phase 2
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7059	Intermediate Similarity	NPD5174	Approved
0.7059	Intermediate Similarity	NPD5175	Approved
0.703	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD4695	Discontinued
0.6979	Remote Similarity	NPD4096	Approved
0.6957	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6881	Approved
0.6952	Remote Similarity	NPD7320	Approved
0.6952	Remote Similarity	NPD6899	Approved
0.6947	Remote Similarity	NPD6903	Approved
0.6947	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6404	Discontinued
0.6931	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD4768	Approved
0.6923	Remote Similarity	NPD4767	Approved
0.6923	Remote Similarity	NPD4692	Approved
0.6909	Remote Similarity	NPD7115	Discovery
0.6907	Remote Similarity	NPD6050	Approved
0.6893	Remote Similarity	NPD4754	Approved
0.6889	Remote Similarity	NPD4195	Approved
0.6887	Remote Similarity	NPD6372	Approved
0.6887	Remote Similarity	NPD6373	Approved
0.6875	Remote Similarity	NPD6904	Approved
0.6875	Remote Similarity	NPD6673	Approved
0.6875	Remote Similarity	NPD6080	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6857	Remote Similarity	NPD6412	Phase 2
0.6857	Remote Similarity	NPD5701	Approved
0.6837	Remote Similarity	NPD5133	Approved
0.6832	Remote Similarity	NPD7638	Approved
0.6822	Remote Similarity	NPD7290	Approved
0.6822	Remote Similarity	NPD6883	Approved
0.6822	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD6942	Approved
0.6818	Remote Similarity	NPD7339	Approved
0.6813	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5692	Phase 3
0.6796	Remote Similarity	NPD5091	Approved
0.6792	Remote Similarity	NPD4730	Approved
0.6792	Remote Similarity	NPD4729	Approved
0.6792	Remote Similarity	NPD5128	Approved
0.6771	Remote Similarity	NPD4518	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6759	Remote Similarity	NPD6617	Approved
0.6759	Remote Similarity	NPD6869	Approved
0.6759	Remote Similarity	NPD6649	Approved
0.6759	Remote Similarity	NPD6847	Approved
0.6759	Remote Similarity	NPD6650	Approved
0.6759	Remote Similarity	NPD8130	Phase 1
0.6735	Remote Similarity	NPD5694	Approved
0.6735	Remote Similarity	NPD7637	Suspended
0.6735	Remote Similarity	NPD5693	Phase 1
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6701	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6882	Approved
0.6697	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6634	Remote Similarity	NPD7614	Phase 1
0.6633	Remote Similarity	NPD5785	Approved
0.6633	Remote Similarity	NPD5207	Approved
0.6632	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5363	Approved
0.663	Remote Similarity	NPD7525	Registered
0.663	Remote Similarity	NPD7514	Phase 3
0.6606	Remote Similarity	NPD5215	Approved
0.6606	Remote Similarity	NPD5217	Approved
0.6606	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5216	Approved
0.6598	Remote Similarity	NPD5208	Approved
0.6596	Remote Similarity	NPD5362	Discontinued
0.6593	Remote Similarity	NPD7145	Approved
0.6569	Remote Similarity	NPD7902	Approved
0.6562	Remote Similarity	NPD6098	Approved
0.6559	Remote Similarity	NPD8028	Phase 2
0.6559	Remote Similarity	NPD6902	Approved
0.6556	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6929	Approved
0.6514	Remote Similarity	NPD5135	Approved
0.6514	Remote Similarity	NPD5169	Approved
0.6514	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4270	Approved
0.6489	Remote Similarity	NPD4269	Approved
0.6489	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4243	Approved
0.6458	Remote Similarity	NPD1696	Phase 3
0.6455	Remote Similarity	NPD5127	Approved
0.6452	Remote Similarity	NPD4252	Approved
0.6452	Remote Similarity	NPD6931	Approved
0.6452	Remote Similarity	NPD6930	Phase 2
0.6452	Remote Similarity	NPD7332	Phase 2
0.6444	Remote Similarity	NPD8264	Approved
0.6437	Remote Similarity	NPD6923	Approved
0.6437	Remote Similarity	NPD6922	Approved
0.6436	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6695	Phase 3
0.642	Remote Similarity	NPD287	Approved
0.6413	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6411	Approved
0.6396	Remote Similarity	NPD6053	Discontinued
0.6373	Remote Similarity	NPD5654	Approved
0.6372	Remote Similarity	NPD6274	Approved
0.6372	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD7144	Approved
0.6364	Remote Similarity	NPD7143	Approved
0.6364	Remote Similarity	NPD4789	Approved
0.6354	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3171	Clinical (unspecified phase)

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