NPASS Compound

Structure

NPC470749 OpenBabel07101718312D 32 34 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 3.8660 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 -0.5000 -0.8660 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 3.5000 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 -3.4641 3.0000 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 -1.7321 0.0000 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 -4.3301 0.5000 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 0.8660 0.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 2 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 24 15 1 1 0 0 0 24 27 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 6 0 0 0 26 29 1 6 0 0 0 26 30 1 0 0 0 0 29 6 1 6 0 0 0 30 7 1 6 0 0 0 30 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.4
Volume:	514.074
LogP:	7.257
LogD:	5.22
LogS:	-6.083
# Rotatable Bonds:	7
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	4.679
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.733
MDCK Permeability:	1.0770765584311448e-05
Pgp-inhibitor:	0.112
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.784

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.392
Plasma Protein Binding (PPB):	90.9601821899414%
Volume Distribution (VD):	1.218
Pgp-substrate:	2.4136204719543457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.235
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.599
CYP2D6-inhibitor:	0.257
CYP2D6-substrate:	0.828
CYP3A4-inhibitor:	0.554
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	5.123
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.864
Carcinogencity:	0.043
Eye Corrosion:	0.042
Eye Irritation:	0.691
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC470749

Natural Product ID:	NPC470749
*Common Name:**	(1R,2R,4As,8As,3'e,1''s)-(+)-1-[6'-(2'',2''-Dimethyl-6''-Methylenecyclohexyl)-4'-Hydroxymethylhex-3'-Enyl]-2,5,5,8A-Tetramethyldecahydronaphthalen-2-Ol
IUPAC Name:	(1R,2R,4aS,8aS)-1-[(E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-(hydroxymethyl)hex-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	WNXNJTRCYLQHHK-BOESEQIKSA-N
Standard InCHI:	InChI=1S/C30H52O2/c1-22-11-9-17-27(2,3)24(22)15-14-23(21-31)12-8-13-26-29(6)19-10-18-28(4,5)25(29)16-20-30(26,7)32/h12,24-26,31-32H,1,8-11,13-21H2,2-7H3/b23-12+/t24-,25+,26-,29+,30-/m1/s1
SMILES:	OC/C(=C/CC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CCCC2(C)C)/CC[C@@H]1C(=C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL220970
PubChem CID:	16109739
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
NPO33073	physeter macrocephalus	Species	Physeteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315955]

☑ 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
ED50	4
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1183	Cell Line	WiDr	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[570183]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[570183]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[570183]
NPT27	Others	Unspecified		ED50	>	10.0	ug ml-1	PMID[570183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	74.4	%	PMID[570183]

☑ 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 NPC470749 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	187
0.1-0.2	1536
0.2-0.3	5754
0.3-0.4	16055
0.4-0.5	8512
0.5-0.6	5556
0.6-0.7	3604
0.7-0.8	1236
0.8-0.85	183
0.85-0.9	60
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC470758
0.9859	High Similarity	NPC470711
0.9714	High Similarity	NPC201048
0.9714	High Similarity	NPC476366
0.9306	High Similarity	NPC32832
0.9211	High Similarity	NPC296701
0.9211	High Similarity	NPC218616
0.92	High Similarity	NPC295131
0.9189	High Similarity	NPC11908
0.9155	High Similarity	NPC167706
0.9054	High Similarity	NPC91594
0.9	High Similarity	NPC94192
0.8933	High Similarity	NPC285761
0.8919	High Similarity	NPC265588
0.8904	High Similarity	NPC100334
0.8904	High Similarity	NPC306727
0.8857	High Similarity	NPC69649
0.8857	High Similarity	NPC68703
0.8846	High Similarity	NPC82623
0.8831	High Similarity	NPC249423
0.8831	High Similarity	NPC476646
0.8816	High Similarity	NPC80530
0.8816	High Similarity	NPC30986
0.8816	High Similarity	NPC209430
0.8816	High Similarity	NPC273410
0.8816	High Similarity	NPC291379
0.88	High Similarity	NPC101475
0.88	High Similarity	NPC90979
0.88	High Similarity	NPC34177
0.88	High Similarity	NPC157996
0.88	High Similarity	NPC40394
0.88	High Similarity	NPC472805
0.8767	High Similarity	NPC474743
0.8767	High Similarity	NPC182717
0.875	High Similarity	NPC34834
0.8732	High Similarity	NPC2648
0.8718	High Similarity	NPC2524
0.8718	High Similarity	NPC304285
0.8718	High Similarity	NPC49964
0.8718	High Similarity	NPC155521
0.8718	High Similarity	NPC87489
0.8701	High Similarity	NPC13554
0.8701	High Similarity	NPC236237
0.8701	High Similarity	NPC322313
0.8701	High Similarity	NPC102253
0.8701	High Similarity	NPC96362
0.8684	High Similarity	NPC474989
0.8684	High Similarity	NPC98386
0.8684	High Similarity	NPC138621
0.8684	High Similarity	NPC167037
0.8684	High Similarity	NPC22955
0.8684	High Similarity	NPC244385
0.8684	High Similarity	NPC230295
0.8684	High Similarity	NPC158662
0.8684	High Similarity	NPC196753
0.8684	High Similarity	NPC6978
0.8684	High Similarity	NPC99168
0.8684	High Similarity	NPC300499
0.8684	High Similarity	NPC470396
0.8684	High Similarity	NPC253807
0.8684	High Similarity	NPC83351
0.8684	High Similarity	NPC167891
0.8684	High Similarity	NPC476314
0.8667	High Similarity	NPC122418
0.8667	High Similarity	NPC237460
0.8667	High Similarity	NPC290598
0.8667	High Similarity	NPC265328
0.8667	High Similarity	NPC253190
0.8667	High Similarity	NPC27765
0.8667	High Similarity	NPC120098
0.8667	High Similarity	NPC30590
0.8649	High Similarity	NPC243342
0.8649	High Similarity	NPC477138
0.8649	High Similarity	NPC91858
0.8649	High Similarity	NPC476736
0.863	High Similarity	NPC23954
0.8611	High Similarity	NPC210323
0.8611	High Similarity	NPC9942
0.8608	High Similarity	NPC134481
0.8608	High Similarity	NPC470558
0.859	High Similarity	NPC264245
0.8571	High Similarity	NPC472463
0.8571	High Similarity	NPC143182
0.8571	High Similarity	NPC53744
0.8571	High Similarity	NPC28862
0.8571	High Similarity	NPC47982
0.8571	High Similarity	NPC84694
0.8571	High Similarity	NPC81306
0.8571	High Similarity	NPC258595
0.8571	High Similarity	NPC109546
0.8553	High Similarity	NPC471798
0.8533	High Similarity	NPC144075
0.8533	High Similarity	NPC291503
0.8533	High Similarity	NPC66566
0.8533	High Similarity	NPC34700
0.8533	High Similarity	NPC477923
0.8533	High Similarity	NPC185536
0.8533	High Similarity	NPC138374
0.8519	High Similarity	NPC261266
0.8519	High Similarity	NPC6391
0.8514	High Similarity	NPC220939
0.8514	High Similarity	NPC265485
0.8514	High Similarity	NPC471799
0.85	High Similarity	NPC205845
0.85	High Similarity	NPC470077
0.85	High Similarity	NPC231310
0.85	High Similarity	NPC474047
0.8481	Intermediate Similarity	NPC101462
0.8481	Intermediate Similarity	NPC470049
0.8481	Intermediate Similarity	NPC202389
0.8472	Intermediate Similarity	NPC96484
0.8462	Intermediate Similarity	NPC164840
0.8462	Intermediate Similarity	NPC241290
0.8462	Intermediate Similarity	NPC209944
0.8462	Intermediate Similarity	NPC234193
0.8462	Intermediate Similarity	NPC281880
0.8451	Intermediate Similarity	NPC476406
0.8442	Intermediate Similarity	NPC312328
0.8442	Intermediate Similarity	NPC472342
0.8442	Intermediate Similarity	NPC72507
0.8442	Intermediate Similarity	NPC85346
0.8442	Intermediate Similarity	NPC474216
0.8442	Intermediate Similarity	NPC301707
0.8442	Intermediate Similarity	NPC65897
0.8442	Intermediate Similarity	NPC302041
0.8442	Intermediate Similarity	NPC472501
0.8421	Intermediate Similarity	NPC106364
0.8421	Intermediate Similarity	NPC189883
0.8421	Intermediate Similarity	NPC247325
0.8421	Intermediate Similarity	NPC106432
0.8421	Intermediate Similarity	NPC244488
0.8415	Intermediate Similarity	NPC470620
0.84	Intermediate Similarity	NPC469593
0.84	Intermediate Similarity	NPC469534
0.84	Intermediate Similarity	NPC471797
0.84	Intermediate Similarity	NPC469533
0.8395	Intermediate Similarity	NPC274448
0.8395	Intermediate Similarity	NPC470360
0.8395	Intermediate Similarity	NPC318390
0.8378	Intermediate Similarity	NPC477792
0.8378	Intermediate Similarity	NPC164022
0.8378	Intermediate Similarity	NPC471272
0.8378	Intermediate Similarity	NPC242001
0.8378	Intermediate Similarity	NPC110799
0.8375	Intermediate Similarity	NPC476927
0.8375	Intermediate Similarity	NPC317458
0.8375	Intermediate Similarity	NPC474634
0.8375	Intermediate Similarity	NPC207013
0.8375	Intermediate Similarity	NPC475789
0.8356	Intermediate Similarity	NPC476431
0.8354	Intermediate Similarity	NPC242350
0.8354	Intermediate Similarity	NPC209620
0.8354	Intermediate Similarity	NPC23852
0.8354	Intermediate Similarity	NPC159148
0.8354	Intermediate Similarity	NPC47761
0.8333	Intermediate Similarity	NPC197805
0.8333	Intermediate Similarity	NPC1319
0.8313	Intermediate Similarity	NPC133588
0.8313	Intermediate Similarity	NPC67872
0.8312	Intermediate Similarity	NPC318495
0.8312	Intermediate Similarity	NPC212241
0.8312	Intermediate Similarity	NPC260301
0.8312	Intermediate Similarity	NPC470751
0.8312	Intermediate Similarity	NPC155986
0.8312	Intermediate Similarity	NPC477924
0.8312	Intermediate Similarity	NPC119355
0.8312	Intermediate Similarity	NPC307336
0.8312	Intermediate Similarity	NPC138502
0.8312	Intermediate Similarity	NPC331618
0.8312	Intermediate Similarity	NPC130136
0.8312	Intermediate Similarity	NPC470750
0.8312	Intermediate Similarity	NPC248830
0.8312	Intermediate Similarity	NPC257191
0.8312	Intermediate Similarity	NPC198968
0.8312	Intermediate Similarity	NPC214570
0.8312	Intermediate Similarity	NPC132542
0.8293	Intermediate Similarity	NPC475069
0.8293	Intermediate Similarity	NPC175145
0.8293	Intermediate Similarity	NPC139724
0.8293	Intermediate Similarity	NPC299068
0.8289	Intermediate Similarity	NPC141071
0.8289	Intermediate Similarity	NPC133580
0.8289	Intermediate Similarity	NPC3403
0.8289	Intermediate Similarity	NPC471723
0.8289	Intermediate Similarity	NPC257347
0.8272	Intermediate Similarity	NPC474493
0.8272	Intermediate Similarity	NPC15534
0.8272	Intermediate Similarity	NPC185568
0.8272	Intermediate Similarity	NPC238485
0.8267	Intermediate Similarity	NPC68443
0.8267	Intermediate Similarity	NPC211009
0.825	Intermediate Similarity	NPC50964
0.825	Intermediate Similarity	NPC248886
0.825	Intermediate Similarity	NPC47763
0.825	Intermediate Similarity	NPC30166
0.825	Intermediate Similarity	NPC189972
0.8243	Intermediate Similarity	NPC92801
0.8243	Intermediate Similarity	NPC45296
0.8243	Intermediate Similarity	NPC145498
0.8228	Intermediate Similarity	NPC236112

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 NPC470749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1770
0.2-0.3	4061
0.3-0.4	2227
0.4-0.5	529
0.5-0.6	200
0.6-0.7	164
0.7-0.8	28
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8701	High Similarity	NPD7525	Registered
0.8571	High Similarity	NPD7645	Phase 2
0.8052	Intermediate Similarity	NPD6942	Approved
0.8052	Intermediate Similarity	NPD7339	Approved
0.7949	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8264	Approved
0.7765	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6924	Approved
0.7692	Intermediate Similarity	NPD6926	Approved
0.7662	Intermediate Similarity	NPD4243	Approved
0.7561	Intermediate Similarity	NPD6931	Approved
0.7561	Intermediate Similarity	NPD6930	Phase 2
0.7531	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6933	Approved
0.7468	Intermediate Similarity	NPD4785	Approved
0.7468	Intermediate Similarity	NPD4784	Approved
0.7442	Intermediate Similarity	NPD3618	Phase 1
0.7439	Intermediate Similarity	NPD6929	Approved
0.7419	Intermediate Similarity	NPD7640	Approved
0.7419	Intermediate Similarity	NPD7639	Approved
0.7416	Intermediate Similarity	NPD7515	Phase 2
0.7412	Intermediate Similarity	NPD4786	Approved
0.7397	Intermediate Similarity	NPD368	Approved
0.7386	Intermediate Similarity	NPD5328	Approved
0.7381	Intermediate Similarity	NPD3667	Approved
0.7349	Intermediate Similarity	NPD7332	Phase 2
0.7349	Intermediate Similarity	NPD7514	Phase 3
0.7349	Intermediate Similarity	NPD7509	Discontinued
0.7312	Intermediate Similarity	NPD7638	Approved
0.7294	Intermediate Similarity	NPD6695	Phase 3
0.7222	Intermediate Similarity	NPD6079	Approved
0.7215	Intermediate Similarity	NPD7151	Approved
0.7215	Intermediate Similarity	NPD7150	Approved
0.7215	Intermediate Similarity	NPD7152	Approved
0.7209	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6925	Approved
0.7195	Intermediate Similarity	NPD5776	Phase 2
0.7179	Intermediate Similarity	NPD6922	Approved
0.7179	Intermediate Similarity	NPD6923	Approved
0.716	Intermediate Similarity	NPD4190	Phase 3
0.716	Intermediate Similarity	NPD5275	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD4748	Discontinued
0.7126	Intermediate Similarity	NPD6893	Approved
0.7126	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7145	Approved
0.7089	Intermediate Similarity	NPD7143	Approved
0.7089	Intermediate Similarity	NPD7144	Approved
0.7065	Intermediate Similarity	NPD7748	Approved
0.7059	Intermediate Similarity	NPD6902	Approved
0.7059	Intermediate Similarity	NPD6898	Phase 1
0.7045	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD4519	Discontinued
0.7042	Intermediate Similarity	NPD342	Phase 1
0.7024	Intermediate Similarity	NPD4195	Approved
0.7011	Intermediate Similarity	NPD3666	Approved
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.6988	Remote Similarity	NPD6932	Approved
0.6966	Remote Similarity	NPD7750	Discontinued
0.6966	Remote Similarity	NPD7524	Approved
0.6962	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD4788	Approved
0.6842	Remote Similarity	NPD7902	Approved
0.6842	Remote Similarity	NPD4755	Approved
0.6824	Remote Similarity	NPD6683	Phase 2
0.6813	Remote Similarity	NPD4753	Phase 2
0.6782	Remote Similarity	NPD4221	Approved
0.6782	Remote Similarity	NPD4223	Phase 3
0.6771	Remote Similarity	NPD4225	Approved
0.6768	Remote Similarity	NPD5141	Approved
0.6742	Remote Similarity	NPD5329	Approved
0.6737	Remote Similarity	NPD5222	Approved
0.6737	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5221	Approved
0.6737	Remote Similarity	NPD4697	Phase 3
0.6735	Remote Similarity	NPD7632	Discontinued
0.6701	Remote Similarity	NPD4700	Approved
0.6701	Remote Similarity	NPD4696	Approved
0.6701	Remote Similarity	NPD5285	Approved
0.6701	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6633	Remote Similarity	NPD5223	Approved
0.663	Remote Similarity	NPD6051	Approved
0.6629	Remote Similarity	NPD3668	Phase 3
0.6629	Remote Similarity	NPD4197	Approved
0.6598	Remote Similarity	NPD5290	Discontinued
0.6596	Remote Similarity	NPD6399	Phase 3
0.6566	Remote Similarity	NPD4633	Approved
0.6566	Remote Similarity	NPD5224	Approved
0.6566	Remote Similarity	NPD5225	Approved
0.6566	Remote Similarity	NPD5226	Approved
0.6556	Remote Similarity	NPD1696	Phase 3
0.6552	Remote Similarity	NPD4695	Discontinued
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6535	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6526	Remote Similarity	NPD7900	Approved
0.6526	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD4754	Approved
0.65	Remote Similarity	NPD5175	Approved
0.6495	Remote Similarity	NPD6084	Phase 2
0.6495	Remote Similarity	NPD6083	Phase 2
0.6489	Remote Similarity	NPD8034	Phase 2
0.6489	Remote Similarity	NPD8035	Phase 2
0.6486	Remote Similarity	NPD4219	Approved
0.6484	Remote Similarity	NPD5205	Approved
0.6484	Remote Similarity	NPD4688	Approved
0.6484	Remote Similarity	NPD5279	Phase 3
0.6484	Remote Similarity	NPD4138	Approved
0.6484	Remote Similarity	NPD4693	Phase 3
0.6484	Remote Similarity	NPD4690	Approved
0.6484	Remote Similarity	NPD4689	Approved
0.6465	Remote Similarity	NPD4159	Approved
0.6458	Remote Similarity	NPD4629	Approved
0.6458	Remote Similarity	NPD5210	Approved
0.6413	Remote Similarity	NPD3573	Approved
0.6408	Remote Similarity	NPD6881	Approved
0.6408	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD6899	Approved
0.6389	Remote Similarity	NPD7115	Discovery
0.6386	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4768	Approved
0.6373	Remote Similarity	NPD4767	Approved
0.6346	Remote Similarity	NPD6372	Approved
0.6346	Remote Similarity	NPD6373	Approved
0.6344	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4723	Approved
0.6344	Remote Similarity	NPD4722	Approved
0.6341	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7328	Approved
0.633	Remote Similarity	NPD7327	Approved
0.6322	Remote Similarity	NPD3617	Approved
0.6316	Remote Similarity	NPD7637	Suspended
0.6311	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD5701	Approved
0.631	Remote Similarity	NPD4732	Discontinued
0.6304	Remote Similarity	NPD4694	Approved
0.6304	Remote Similarity	NPD6684	Approved
0.6304	Remote Similarity	NPD5690	Phase 2
0.6304	Remote Similarity	NPD5280	Approved
0.6304	Remote Similarity	NPD7521	Approved
0.6304	Remote Similarity	NPD7334	Approved
0.6304	Remote Similarity	NPD7146	Approved
0.6304	Remote Similarity	NPD5330	Approved
0.6304	Remote Similarity	NPD6409	Approved
0.6286	Remote Similarity	NPD6883	Approved
0.6286	Remote Similarity	NPD7102	Approved
0.6286	Remote Similarity	NPD7290	Approved
0.6279	Remote Similarity	NPD6117	Approved
0.6277	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6235	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6617	Approved
0.6226	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6650	Approved
0.6226	Remote Similarity	NPD8130	Phase 1
0.6226	Remote Similarity	NPD6649	Approved
0.6226	Remote Similarity	NPD6869	Approved
0.6226	Remote Similarity	NPD6847	Approved
0.6222	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5360	Phase 3
0.622	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8294	Approved
0.6216	Remote Similarity	NPD8377	Approved
0.6211	Remote Similarity	NPD7136	Phase 2
0.6207	Remote Similarity	NPD6116	Phase 1
0.619	Remote Similarity	NPD6014	Approved
0.619	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD6013	Approved
0.617	Remote Similarity	NPD6903	Approved
0.617	Remote Similarity	NPD5737	Approved
0.617	Remote Similarity	NPD6672	Approved
0.6168	Remote Similarity	NPD6882	Approved
0.6168	Remote Similarity	NPD8297	Approved
0.6163	Remote Similarity	NPD3703	Phase 2
0.6161	Remote Similarity	NPD8378	Approved
0.6161	Remote Similarity	NPD8296	Approved
0.6161	Remote Similarity	NPD8380	Approved
0.6161	Remote Similarity	NPD8335	Approved
0.6161	Remote Similarity	NPD8379	Approved
0.6161	Remote Similarity	NPD8033	Approved
0.6146	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD5344	Discontinued
0.6136	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6697	Approved
0.6136	Remote Similarity	NPD6115	Approved
0.6136	Remote Similarity	NPD6118	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