NPASS Compound

Structure

NPC470711 OpenBabel07101718282D 32 34 0 0 1 0 0 0 0 0999 V2000 5.1962 3.0000 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 7.4282 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 0.1340 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 7.7942 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 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 6.9282 1.0000 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 21 2 0 0 0 0 2 22 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 22 2 0 0 0 0 13 21 1 0 0 0 0 14 26 1 0 0 0 0 15 19 1 0 0 0 0 15 25 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 20 1 6 0 0 0 23 27 1 0 0 0 0 24 31 1 6 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 7 1 6 0 0 0 30 8 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:	7.078
LogD:	5.279
LogS:	-6.437
# Rotatable Bonds:	6
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	4.844
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:	-4.735
MDCK Permeability:	1.3112652595737018e-05
Pgp-inhibitor:	0.581
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	93.87728118896484%
Volume Distribution (VD):	1.296
Pgp-substrate:	2.4538862705230713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.345
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.138
CYP2D6-substrate:	0.824
CYP3A4-inhibitor:	0.488
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	5.167
Half-life (T1/2):	0.014

ADMET: Toxicity

hERG Blockers:	0.225
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.357
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.618
Carcinogencity:	0.044
Eye Corrosion:	0.32
Eye Irritation:	0.721
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC470711

Natural Product ID:	NPC470711
*Common Name:**	(1R,2R,4As,8As,3'e,5'r,1''s)-(-)-1-[6'-(2'',2''-Dimethyl-6''-Methylenecyclohexyl)-4'-Methyl-5'-Hydroxyhex-3'-Enyl]-2,5,5,8A-Tetramethyldecahydronaphthalen-2-Ol
IUPAC Name:	(1R,2R,4aS,8aS)-1-[(E,5R)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-5-hydroxy-4-methylhex-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	QXSVGYIHTCMMOA-UDEUFLGDSA-N
Standard InCHI:	InChI=1S/C30H52O2/c1-21-13-10-16-27(3,4)23(21)20-24(31)22(2)12-9-14-26-29(7)18-11-17-28(5,6)25(29)15-19-30(26,8)32/h12,23-26,31-32H,1,9-11,13-20H2,2-8H3/b22-12+/t23-,24-,25+,26-,29+,30-/m1/s1
SMILES:	O[C@@H](/C(=C/CC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CCCC2(C)C)/C)C[C@@H]1C(=C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL220487
PubChem CID:	16109745
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[447425]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[447425]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[447425]
NPT27	Others	Unspecified		ED50	>	10.0	ug ml-1	PMID[447425]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	79.3	%	PMID[447425]

☑ 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 NPC470711 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	191
0.1-0.2	1511
0.2-0.3	5664
0.3-0.4	15493
0.4-0.5	8823
0.5-0.6	5601
0.6-0.7	3739
0.7-0.8	1352
0.8-0.85	227
0.85-0.9	81
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470758
0.9859	High Similarity	NPC470749
0.9577	High Similarity	NPC201048
0.9577	High Similarity	NPC476366
0.9342	High Similarity	NPC218616
0.9342	High Similarity	NPC296701
0.9333	High Similarity	NPC295131
0.9324	High Similarity	NPC11908
0.9296	High Similarity	NPC167706
0.9189	High Similarity	NPC91594
0.9178	High Similarity	NPC32832
0.9067	High Similarity	NPC285761
0.9054	High Similarity	NPC265588
0.9041	High Similarity	NPC100334
0.9041	High Similarity	NPC306727
0.8974	High Similarity	NPC82623
0.8961	High Similarity	NPC476646
0.8961	High Similarity	NPC249423
0.8947	High Similarity	NPC273410
0.8947	High Similarity	NPC291379
0.8947	High Similarity	NPC80530
0.8947	High Similarity	NPC30986
0.8947	High Similarity	NPC209430
0.8933	High Similarity	NPC101475
0.8933	High Similarity	NPC40394
0.8933	High Similarity	NPC34177
0.8933	High Similarity	NPC472805
0.8933	High Similarity	NPC157996
0.8933	High Similarity	NPC90979
0.8904	High Similarity	NPC182717
0.8889	High Similarity	NPC34834
0.8873	High Similarity	NPC94192
0.8846	High Similarity	NPC304285
0.8846	High Similarity	NPC87489
0.8846	High Similarity	NPC155521
0.8846	High Similarity	NPC49964
0.8831	High Similarity	NPC322313
0.8831	High Similarity	NPC96362
0.8831	High Similarity	NPC102253
0.8831	High Similarity	NPC236237
0.8831	High Similarity	NPC13554
0.8816	High Similarity	NPC470396
0.8816	High Similarity	NPC253807
0.8816	High Similarity	NPC83351
0.8816	High Similarity	NPC300499
0.8816	High Similarity	NPC476314
0.8816	High Similarity	NPC167891
0.8816	High Similarity	NPC167037
0.8816	High Similarity	NPC158662
0.8816	High Similarity	NPC6978
0.8816	High Similarity	NPC22955
0.8816	High Similarity	NPC196753
0.8816	High Similarity	NPC138621
0.8816	High Similarity	NPC244385
0.8816	High Similarity	NPC230295
0.8816	High Similarity	NPC98386
0.8816	High Similarity	NPC474989
0.8816	High Similarity	NPC99168
0.88	High Similarity	NPC27765
0.88	High Similarity	NPC290598
0.88	High Similarity	NPC237460
0.88	High Similarity	NPC253190
0.88	High Similarity	NPC122418
0.88	High Similarity	NPC265328
0.88	High Similarity	NPC30590
0.88	High Similarity	NPC120098
0.8784	High Similarity	NPC477138
0.8784	High Similarity	NPC91858
0.8784	High Similarity	NPC243342
0.8767	High Similarity	NPC23954
0.875	High Similarity	NPC210323
0.875	High Similarity	NPC9942
0.8734	High Similarity	NPC470558
0.8734	High Similarity	NPC134481
0.8732	High Similarity	NPC68703
0.8732	High Similarity	NPC69649
0.8718	High Similarity	NPC264245
0.8701	High Similarity	NPC81306
0.8701	High Similarity	NPC53744
0.8701	High Similarity	NPC109546
0.8701	High Similarity	NPC472463
0.8701	High Similarity	NPC143182
0.8701	High Similarity	NPC84694
0.8701	High Similarity	NPC28862
0.8701	High Similarity	NPC47982
0.8684	High Similarity	NPC471798
0.8667	High Similarity	NPC66566
0.8667	High Similarity	NPC477923
0.8667	High Similarity	NPC185536
0.8667	High Similarity	NPC291503
0.8667	High Similarity	NPC34700
0.8667	High Similarity	NPC144075
0.8667	High Similarity	NPC138374
0.8649	High Similarity	NPC474743
0.8649	High Similarity	NPC265485
0.8649	High Similarity	NPC471799
0.8649	High Similarity	NPC220939
0.8642	High Similarity	NPC6391
0.8642	High Similarity	NPC261266
0.8625	High Similarity	NPC470077
0.8625	High Similarity	NPC231310
0.8625	High Similarity	NPC205845
0.8625	High Similarity	NPC474047
0.8611	High Similarity	NPC2648
0.8611	High Similarity	NPC96484
0.8608	High Similarity	NPC470049
0.8608	High Similarity	NPC2524
0.8608	High Similarity	NPC202389
0.8608	High Similarity	NPC101462
0.859	High Similarity	NPC209944
0.859	High Similarity	NPC281880
0.859	High Similarity	NPC241290
0.859	High Similarity	NPC164840
0.859	High Similarity	NPC234193
0.8571	High Similarity	NPC302041
0.8571	High Similarity	NPC85346
0.8571	High Similarity	NPC472501
0.8571	High Similarity	NPC472342
0.8571	High Similarity	NPC312328
0.8571	High Similarity	NPC474216
0.8571	High Similarity	NPC301707
0.8571	High Similarity	NPC65897
0.8571	High Similarity	NPC72507
0.8553	High Similarity	NPC247325
0.8553	High Similarity	NPC244488
0.8553	High Similarity	NPC106432
0.8553	High Similarity	NPC106364
0.8553	High Similarity	NPC189883
0.8537	High Similarity	NPC470620
0.8533	High Similarity	NPC469534
0.8533	High Similarity	NPC469593
0.8533	High Similarity	NPC476736
0.8533	High Similarity	NPC469533
0.8533	High Similarity	NPC471797
0.8519	High Similarity	NPC470360
0.8519	High Similarity	NPC274448
0.8519	High Similarity	NPC318390
0.8514	High Similarity	NPC477792
0.8514	High Similarity	NPC242001
0.8514	High Similarity	NPC110799
0.8514	High Similarity	NPC471272
0.8514	High Similarity	NPC164022
0.85	High Similarity	NPC207013
0.85	High Similarity	NPC474634
0.85	High Similarity	NPC317458
0.85	High Similarity	NPC475789
0.8481	Intermediate Similarity	NPC209620
0.8481	Intermediate Similarity	NPC159148
0.8481	Intermediate Similarity	NPC242350
0.8481	Intermediate Similarity	NPC47761
0.8481	Intermediate Similarity	NPC23852
0.8462	Intermediate Similarity	NPC1319
0.8451	Intermediate Similarity	NPC258595
0.8442	Intermediate Similarity	NPC257191
0.8442	Intermediate Similarity	NPC119355
0.8442	Intermediate Similarity	NPC198968
0.8442	Intermediate Similarity	NPC130136
0.8442	Intermediate Similarity	NPC138502
0.8442	Intermediate Similarity	NPC260301
0.8442	Intermediate Similarity	NPC248830
0.8442	Intermediate Similarity	NPC318495
0.8442	Intermediate Similarity	NPC212241
0.8442	Intermediate Similarity	NPC307336
0.8442	Intermediate Similarity	NPC214570
0.8442	Intermediate Similarity	NPC470751
0.8442	Intermediate Similarity	NPC155986
0.8442	Intermediate Similarity	NPC470750
0.8442	Intermediate Similarity	NPC477924
0.8442	Intermediate Similarity	NPC331618
0.8434	Intermediate Similarity	NPC67872
0.8434	Intermediate Similarity	NPC133588
0.8421	Intermediate Similarity	NPC133580
0.8421	Intermediate Similarity	NPC3403
0.8421	Intermediate Similarity	NPC257347
0.8421	Intermediate Similarity	NPC141071
0.8421	Intermediate Similarity	NPC471723
0.8415	Intermediate Similarity	NPC299068
0.8415	Intermediate Similarity	NPC175145
0.8415	Intermediate Similarity	NPC139724
0.8415	Intermediate Similarity	NPC475069
0.84	Intermediate Similarity	NPC211009
0.84	Intermediate Similarity	NPC68443
0.8395	Intermediate Similarity	NPC474493
0.8395	Intermediate Similarity	NPC185568
0.8395	Intermediate Similarity	NPC238485
0.8378	Intermediate Similarity	NPC92801
0.8378	Intermediate Similarity	NPC45296
0.8378	Intermediate Similarity	NPC145498
0.8375	Intermediate Similarity	NPC189972
0.8375	Intermediate Similarity	NPC248886
0.8375	Intermediate Similarity	NPC47763
0.8375	Intermediate Similarity	NPC30166
0.8375	Intermediate Similarity	NPC50964
0.8356	Intermediate Similarity	NPC471238
0.8356	Intermediate Similarity	NPC208999
0.8356	Intermediate Similarity	NPC245795
0.8356	Intermediate Similarity	NPC276616
0.8354	Intermediate Similarity	NPC236112
0.8333	Intermediate Similarity	NPC148977
0.8333	Intermediate Similarity	NPC476406

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 NPC470711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1757
0.2-0.3	4063
0.3-0.4	2209
0.4-0.5	546
0.5-0.6	193
0.6-0.7	177
0.7-0.8	31
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8831	High Similarity	NPD7525	Registered
0.8701	High Similarity	NPD7645	Phase 2
0.8182	Intermediate Similarity	NPD6942	Approved
0.8182	Intermediate Similarity	NPD7339	Approved
0.8077	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD8264	Approved
0.7882	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6926	Approved
0.7821	Intermediate Similarity	NPD6924	Approved
0.7683	Intermediate Similarity	NPD6930	Phase 2
0.7683	Intermediate Similarity	NPD6931	Approved
0.7654	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6933	Approved
0.7564	Intermediate Similarity	NPD4243	Approved
0.7561	Intermediate Similarity	NPD6929	Approved
0.7558	Intermediate Similarity	NPD3618	Phase 1
0.7534	Intermediate Similarity	NPD368	Approved
0.7529	Intermediate Similarity	NPD4786	Approved
0.7528	Intermediate Similarity	NPD7515	Phase 2
0.7527	Intermediate Similarity	NPD7639	Approved
0.7527	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.747	Intermediate Similarity	NPD7509	Discontinued
0.747	Intermediate Similarity	NPD7332	Phase 2
0.747	Intermediate Similarity	NPD7514	Phase 3
0.7419	Intermediate Similarity	NPD7638	Approved
0.7412	Intermediate Similarity	NPD6695	Phase 3
0.7375	Intermediate Similarity	NPD4785	Approved
0.7375	Intermediate Similarity	NPD4784	Approved
0.7342	Intermediate Similarity	NPD7150	Approved
0.7342	Intermediate Similarity	NPD7151	Approved
0.7342	Intermediate Similarity	NPD7152	Approved
0.7333	Intermediate Similarity	NPD6079	Approved
0.7326	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6925	Approved
0.7317	Intermediate Similarity	NPD5776	Phase 2
0.7308	Intermediate Similarity	NPD6922	Approved
0.7308	Intermediate Similarity	NPD6923	Approved
0.7262	Intermediate Similarity	NPD4748	Discontinued
0.7253	Intermediate Similarity	NPD4202	Approved
0.7241	Intermediate Similarity	NPD6893	Approved
0.7241	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7145	Approved
0.7215	Intermediate Similarity	NPD7144	Approved
0.7215	Intermediate Similarity	NPD7143	Approved
0.7176	Intermediate Similarity	NPD6902	Approved
0.7176	Intermediate Similarity	NPD6898	Phase 1
0.7174	Intermediate Similarity	NPD7748	Approved
0.7126	Intermediate Similarity	NPD3666	Approved
0.7126	Intermediate Similarity	NPD3665	Phase 1
0.7126	Intermediate Similarity	NPD3133	Approved
0.7108	Intermediate Similarity	NPD6932	Approved
0.7089	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7524	Approved
0.7079	Intermediate Similarity	NPD7750	Discontinued
0.7073	Intermediate Similarity	NPD5275	Approved
0.7073	Intermediate Similarity	NPD4190	Phase 3
0.701	Intermediate Similarity	NPD5211	Phase 2
0.6966	Remote Similarity	NPD4623	Approved
0.6966	Remote Similarity	NPD4519	Discontinued
0.6947	Remote Similarity	NPD4755	Approved
0.6947	Remote Similarity	NPD7902	Approved
0.6944	Remote Similarity	NPD342	Phase 1
0.6941	Remote Similarity	NPD4195	Approved
0.6941	Remote Similarity	NPD6683	Phase 2
0.6875	Remote Similarity	NPD4225	Approved
0.6869	Remote Similarity	NPD5141	Approved
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6837	Remote Similarity	NPD7632	Discontinued
0.6818	Remote Similarity	NPD4788	Approved
0.6804	Remote Similarity	NPD4700	Approved
0.6804	Remote Similarity	NPD5286	Approved
0.6804	Remote Similarity	NPD4696	Approved
0.6804	Remote Similarity	NPD5285	Approved
0.679	Remote Similarity	NPD4787	Phase 1
0.6774	Remote Similarity	NPD7087	Discontinued
0.6771	Remote Similarity	NPD5173	Approved
0.6742	Remote Similarity	NPD3668	Phase 3
0.6739	Remote Similarity	NPD6051	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6735	Remote Similarity	NPD5223	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6705	Remote Similarity	NPD4221	Approved
0.6702	Remote Similarity	NPD6399	Phase 3
0.6701	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6634	Remote Similarity	NPD6402	Approved
0.6634	Remote Similarity	NPD5739	Approved
0.6634	Remote Similarity	NPD7128	Approved
0.6634	Remote Similarity	NPD6675	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7900	Approved
0.66	Remote Similarity	NPD5175	Approved
0.66	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD5174	Approved
0.6596	Remote Similarity	NPD8034	Phase 2
0.6596	Remote Similarity	NPD8035	Phase 2
0.6593	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5279	Phase 3
0.6566	Remote Similarity	NPD4159	Approved
0.6556	Remote Similarity	NPD4197	Approved
0.6506	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.6505	Remote Similarity	NPD7320	Approved
0.6484	Remote Similarity	NPD1696	Phase 3
0.6481	Remote Similarity	NPD7115	Discovery
0.6477	Remote Similarity	NPD4695	Discontinued
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6463	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6372	Approved
0.6442	Remote Similarity	NPD6373	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD4732	Discontinued
0.6429	Remote Similarity	NPD6084	Phase 2
0.6422	Remote Similarity	NPD7328	Approved
0.6422	Remote Similarity	NPD7327	Approved
0.6421	Remote Similarity	NPD7637	Suspended
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD4689	Approved
0.6413	Remote Similarity	NPD7521	Approved
0.6413	Remote Similarity	NPD7334	Approved
0.6413	Remote Similarity	NPD6409	Approved
0.6413	Remote Similarity	NPD6684	Approved
0.6413	Remote Similarity	NPD7146	Approved
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD4688	Approved
0.6413	Remote Similarity	NPD5330	Approved
0.6408	Remote Similarity	NPD5701	Approved
0.6408	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD4219	Approved
0.6395	Remote Similarity	NPD6117	Approved
0.6392	Remote Similarity	NPD5210	Approved
0.6392	Remote Similarity	NPD4629	Approved
0.6381	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD7516	Approved
0.6353	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5128	Approved
0.6346	Remote Similarity	NPD6011	Approved
0.6346	Remote Similarity	NPD4730	Approved
0.6346	Remote Similarity	NPD4729	Approved
0.6344	Remote Similarity	NPD3573	Approved
0.6322	Remote Similarity	NPD6116	Phase 1
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8130	Phase 1
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD6847	Approved
0.6316	Remote Similarity	NPD7136	Phase 2
0.6306	Remote Similarity	NPD8294	Approved
0.6306	Remote Similarity	NPD8377	Approved
0.6286	Remote Similarity	NPD6014	Approved
0.6286	Remote Similarity	NPD6013	Approved
0.6286	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD3703	Phase 2
0.6277	Remote Similarity	NPD4722	Approved
0.6277	Remote Similarity	NPD4723	Approved
0.6277	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD6118	Approved
0.625	Remote Similarity	NPD6115	Approved
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD3617	Approved
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD6697	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD6114	Approved
0.6238	Remote Similarity	NPD5344	Discontinued
0.6237	Remote Similarity	NPD4694	Approved
0.6237	Remote Similarity	NPD5690	Phase 2
0.6237	Remote Similarity	NPD5280	Approved
0.6226	Remote Similarity	NPD5249	Phase 3
0.6226	Remote Similarity	NPD5251	Approved
0.6226	Remote Similarity	NPD5135	Approved
0.6226	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4634	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