NPASS Compound

Structure

CID167706 OpenBabel06191715542D 32 33 0 0 1 0 0 0 0 0999 V2000 0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 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 -0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 0.0000 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 0 0 0 0 0 0 0 0 0 0 0.0000 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -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 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 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 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 22 2 0 0 0 0 13 23 1 0 0 0 0 14 23 2 0 0 0 0 15 24 1 0 0 0 0 16 24 2 0 0 0 0 17 26 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 29 1 0 0 0 0 21 30 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 27 28 1 0 0 0 0 27 31 1 6 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:	519.994
LogP:	7.503
LogD:	5.713
LogS:	-5.916
# Rotatable Bonds:	9
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	4.415
Fsp3:	0.8
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:	-4.764
MDCK Permeability:	1.7654318071436137e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.384
Plasma Protein Binding (PPB):	96.40196228027344%
Volume Distribution (VD):	1.799
Pgp-substrate:	4.45540189743042%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.239
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.425
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	6.569
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.003
AMES Toxicity:	0.0
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.941
Carcinogencity:	0.005
Eye Corrosion:	0.502
Eye Irritation:	0.6
Respiratory Toxicity:	0.165

Download Data

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

Natural Product: NPC167706

Natural Product ID:	NPC167706
*Common Name:**	(2S,4As,5R,6R,8Ar)-1,1,4A,6-Tetramethyl-5-((3E,7E)-4,8,12-Trimethyltrideca-3,7,11-Trienyl)Decahydronaphthalene-2,6-Diol
IUPAC Name:	(1R,2R,4aR,6S,8aS)-2,5,5,8a-tetramethyl-1-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,6-diol
Synonyms:
Standard InCHIKey:	QGERZRKJXVVRQA-NJACTVBXSA-N
Standard InCHI:	InChI=1S/C30H52O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-26-29(7)20-19-27(31)28(5,6)25(29)18-21-30(26,8)32/h12,14,16,25-27,31-32H,9-11,13,15,17-21H2,1-8H3/b23-14+,24-16+/t25-,26+,27-,29-,30+/m0/s1
SMILES:	C/C(=CCC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1916182
PubChem CID:	57401582
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
NPO11772	Pistacia lentiscus	Species	Anacardiaceae	Eukaryota	n.a.	latex	n.a.	PMID[21800858]
NPO25991	Commiphora mukul	Species	Burseraceae	Eukaryota	n.a.	latex	n.a.	PMID[21800858]
NPO25991	Commiphora mukul	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25991	Commiphora mukul	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11772	Pistacia lentiscus	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21797	Derris brevipes	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25991	Commiphora mukul	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11772	Pistacia lentiscus	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15081	Aleuroglyphus ovatus	Species	Acaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17642	Chondropetalum paniculatum	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	2
Others	6

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	75.4	%	PMID[450777]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	74.2	%	PMID[450777]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	5.6	%	PMID[450777]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	9.3	%	PMID[450777]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	18.9	%	PMID[450777]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	17.3	%	PMID[450777]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	30000.0	nM	PMID[450777]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	4000.0	nM	PMID[450777]

☑ 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 NPC167706 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	172
0.1-0.2	1491
0.2-0.3	6574
0.3-0.4	16134
0.4-0.5	7653
0.5-0.6	5742
0.6-0.7	3438
0.7-0.8	1151
0.8-0.85	223
0.85-0.9	91
0.9-0.95	27
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.942	High Similarity	NPC201048
0.942	High Similarity	NPC476366
0.9296	High Similarity	NPC470711
0.9296	High Similarity	NPC470758
0.9275	High Similarity	NPC182717
0.9167	High Similarity	NPC285761
0.9155	High Similarity	NPC470749
0.9155	High Similarity	NPC265588
0.9143	High Similarity	NPC243342
0.9143	High Similarity	NPC100334
0.9143	High Similarity	NPC91858
0.9143	High Similarity	NPC477138
0.913	High Similarity	NPC164022
0.9041	High Similarity	NPC80530
0.9041	High Similarity	NPC291379
0.9041	High Similarity	NPC273410
0.9028	High Similarity	NPC157996
0.9028	High Similarity	NPC471798
0.9028	High Similarity	NPC472805
0.9028	High Similarity	NPC101475
0.9028	High Similarity	NPC40394
0.9028	High Similarity	NPC34177
0.9028	High Similarity	NPC90979
0.9014	High Similarity	NPC66566
0.9014	High Similarity	NPC291503
0.9014	High Similarity	NPC32832
0.9014	High Similarity	NPC477923
0.9	High Similarity	NPC471799
0.9	High Similarity	NPC68443
0.8986	High Similarity	NPC92801
0.8971	High Similarity	NPC208999
0.8971	High Similarity	NPC94192
0.8939	High Similarity	NPC101128
0.8939	High Similarity	NPC225415
0.8919	High Similarity	NPC13554
0.8919	High Similarity	NPC322313
0.8919	High Similarity	NPC102253
0.8919	High Similarity	NPC236237
0.8904	High Similarity	NPC98386
0.8904	High Similarity	NPC22955
0.8904	High Similarity	NPC196753
0.8904	High Similarity	NPC6978
0.8904	High Similarity	NPC474989
0.8904	High Similarity	NPC167037
0.8904	High Similarity	NPC158662
0.8904	High Similarity	NPC99168
0.8904	High Similarity	NPC138621
0.8904	High Similarity	NPC470396
0.8904	High Similarity	NPC253807
0.8904	High Similarity	NPC300499
0.8904	High Similarity	NPC230295
0.8904	High Similarity	NPC244385
0.8889	High Similarity	NPC106432
0.8889	High Similarity	NPC122418
0.8889	High Similarity	NPC120098
0.8889	High Similarity	NPC265328
0.8889	High Similarity	NPC27765
0.8889	High Similarity	NPC189883
0.8889	High Similarity	NPC290598
0.8889	High Similarity	NPC237460
0.8889	High Similarity	NPC30590
0.8873	High Similarity	NPC471797
0.8873	High Similarity	NPC306727
0.8857	High Similarity	NPC242001
0.8857	High Similarity	NPC110799
0.8841	High Similarity	NPC210323
0.8841	High Similarity	NPC476431
0.8841	High Similarity	NPC9942
0.8824	High Similarity	NPC185874
0.8824	High Similarity	NPC269077
0.8824	High Similarity	NPC253303
0.8824	High Similarity	NPC139207
0.8784	High Similarity	NPC472463
0.8784	High Similarity	NPC53744
0.8784	High Similarity	NPC1319
0.8767	High Similarity	NPC198968
0.8767	High Similarity	NPC214570
0.8767	High Similarity	NPC130136
0.8767	High Similarity	NPC155986
0.8767	High Similarity	NPC477924
0.8767	High Similarity	NPC318495
0.8767	High Similarity	NPC91594
0.875	High Similarity	NPC138374
0.875	High Similarity	NPC141071
0.875	High Similarity	NPC34700
0.875	High Similarity	NPC257347
0.875	High Similarity	NPC471723
0.8714	High Similarity	NPC34834
0.8714	High Similarity	NPC145498
0.8696	High Similarity	NPC2648
0.8696	High Similarity	NPC244790
0.8684	High Similarity	NPC296701
0.8684	High Similarity	NPC155521
0.8684	High Similarity	NPC218616
0.8684	High Similarity	NPC30166
0.8667	High Similarity	NPC236112
0.8667	High Similarity	NPC295131
0.8657	High Similarity	NPC144650
0.8649	High Similarity	NPC65897
0.8649	High Similarity	NPC312328
0.8649	High Similarity	NPC275910
0.8649	High Similarity	NPC85346
0.8649	High Similarity	NPC72507
0.8649	High Similarity	NPC302041
0.8649	High Similarity	NPC11908
0.863	High Similarity	NPC134330
0.863	High Similarity	NPC274079
0.863	High Similarity	NPC129165
0.863	High Similarity	NPC321016
0.863	High Similarity	NPC300324
0.863	High Similarity	NPC46160
0.863	High Similarity	NPC106364
0.863	High Similarity	NPC107059
0.863	High Similarity	NPC477925
0.863	High Similarity	NPC240604
0.863	High Similarity	NPC1973
0.863	High Similarity	NPC63958
0.863	High Similarity	NPC321381
0.863	High Similarity	NPC167873
0.863	High Similarity	NPC202642
0.863	High Similarity	NPC73875
0.8592	High Similarity	NPC242992
0.8592	High Similarity	NPC23954
0.8571	High Similarity	NPC207013
0.8553	High Similarity	NPC476646
0.8553	High Similarity	NPC474531
0.8553	High Similarity	NPC249423
0.8553	High Similarity	NPC242350
0.8551	High Similarity	NPC68703
0.8551	High Similarity	NPC69649
0.8551	High Similarity	NPC197805
0.8533	High Similarity	NPC209430
0.8533	High Similarity	NPC30986
0.8533	High Similarity	NPC328714
0.8529	High Similarity	NPC208198
0.8529	High Similarity	NPC2728
0.8529	High Similarity	NPC60837
0.8529	High Similarity	NPC258595
0.8529	High Similarity	NPC172613
0.8529	High Similarity	NPC282619
0.8529	High Similarity	NPC64123
0.8529	High Similarity	NPC11555
0.8514	High Similarity	NPC470428
0.8493	Intermediate Similarity	NPC285893
0.8493	Intermediate Similarity	NPC118508
0.8493	Intermediate Similarity	NPC28657
0.8493	Intermediate Similarity	NPC288035
0.8493	Intermediate Similarity	NPC230301
0.8493	Intermediate Similarity	NPC121744
0.8493	Intermediate Similarity	NPC162742
0.8493	Intermediate Similarity	NPC3403
0.8493	Intermediate Similarity	NPC322353
0.8493	Intermediate Similarity	NPC22105
0.8493	Intermediate Similarity	NPC134847
0.8493	Intermediate Similarity	NPC136188
0.8493	Intermediate Similarity	NPC304309
0.8472	Intermediate Similarity	NPC265485
0.8472	Intermediate Similarity	NPC474140
0.8472	Intermediate Similarity	NPC211009
0.8472	Intermediate Similarity	NPC220939
0.8462	Intermediate Similarity	NPC470077
0.8462	Intermediate Similarity	NPC474493
0.8451	Intermediate Similarity	NPC45296
0.8442	Intermediate Similarity	NPC87489
0.8442	Intermediate Similarity	NPC47763
0.8442	Intermediate Similarity	NPC248886
0.8442	Intermediate Similarity	NPC49964
0.8442	Intermediate Similarity	NPC470049
0.8442	Intermediate Similarity	NPC304285
0.8442	Intermediate Similarity	NPC2524
0.8429	Intermediate Similarity	NPC245795
0.8429	Intermediate Similarity	NPC160209
0.8429	Intermediate Similarity	NPC276616
0.8429	Intermediate Similarity	NPC96484
0.8421	Intermediate Similarity	NPC241290
0.8421	Intermediate Similarity	NPC164840
0.8421	Intermediate Similarity	NPC209944
0.8421	Intermediate Similarity	NPC287749
0.8421	Intermediate Similarity	NPC281880
0.8421	Intermediate Similarity	NPC96362
0.8406	Intermediate Similarity	NPC222366
0.8406	Intermediate Similarity	NPC149680
0.8406	Intermediate Similarity	NPC476406
0.8406	Intermediate Similarity	NPC473929
0.8406	Intermediate Similarity	NPC476039
0.8406	Intermediate Similarity	NPC286669
0.84	Intermediate Similarity	NPC476314
0.84	Intermediate Similarity	NPC87604
0.84	Intermediate Similarity	NPC473943
0.84	Intermediate Similarity	NPC205455
0.84	Intermediate Similarity	NPC476949
0.84	Intermediate Similarity	NPC83351
0.84	Intermediate Similarity	NPC167891
0.84	Intermediate Similarity	NPC148977
0.84	Intermediate Similarity	NPC477522
0.84	Intermediate Similarity	NPC318136
0.84	Intermediate Similarity	NPC186191
0.84	Intermediate Similarity	NPC474216
0.8382	Intermediate Similarity	NPC290367
0.8382	Intermediate Similarity	NPC68656

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 NPC167706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1857
0.2-0.3	4136
0.3-0.4	2132
0.4-0.5	481
0.5-0.6	187
0.6-0.7	155
0.7-0.8	41
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD7525	Registered
0.8784	High Similarity	NPD7645	Phase 2
0.8493	Intermediate Similarity	NPD7339	Approved
0.8493	Intermediate Similarity	NPD6942	Approved
0.8378	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD6924	Approved
0.8356	Intermediate Similarity	NPD6926	Approved
0.8133	Intermediate Similarity	NPD6933	Approved
0.7949	Intermediate Similarity	NPD7509	Discontinued
0.7838	Intermediate Similarity	NPD7152	Approved
0.7838	Intermediate Similarity	NPD4243	Approved
0.7838	Intermediate Similarity	NPD7150	Approved
0.7838	Intermediate Similarity	NPD7151	Approved
0.7808	Intermediate Similarity	NPD6923	Approved
0.7808	Intermediate Similarity	NPD6922	Approved
0.7805	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD4786	Approved
0.7763	Intermediate Similarity	NPD8264	Approved
0.775	Intermediate Similarity	NPD3667	Approved
0.7738	Intermediate Similarity	NPD5328	Approved
0.7722	Intermediate Similarity	NPD6930	Phase 2
0.7722	Intermediate Similarity	NPD6931	Approved
0.7703	Intermediate Similarity	NPD7144	Approved
0.7703	Intermediate Similarity	NPD7143	Approved
0.7632	Intermediate Similarity	NPD4784	Approved
0.7632	Intermediate Similarity	NPD4785	Approved
0.7595	Intermediate Similarity	NPD6929	Approved
0.7564	Intermediate Similarity	NPD6932	Approved
0.7558	Intermediate Similarity	NPD7515	Phase 2
0.7558	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD4748	Discontinued
0.75	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4202	Approved
0.7468	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6695	Phase 3
0.7375	Intermediate Similarity	NPD6683	Phase 2
0.7349	Intermediate Similarity	NPD3665	Phase 1
0.7349	Intermediate Similarity	NPD3133	Approved
0.7349	Intermediate Similarity	NPD3666	Approved
0.7349	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6925	Approved
0.7342	Intermediate Similarity	NPD5776	Phase 2
0.7324	Intermediate Similarity	NPD368	Approved
0.7308	Intermediate Similarity	NPD5275	Approved
0.7308	Intermediate Similarity	NPD4190	Phase 3
0.7284	Intermediate Similarity	NPD7514	Phase 3
0.7284	Intermediate Similarity	NPD7332	Phase 2
0.7262	Intermediate Similarity	NPD6893	Approved
0.7262	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7145	Approved
0.7195	Intermediate Similarity	NPD6898	Phase 1
0.7191	Intermediate Similarity	NPD7748	Approved
0.716	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD4755	Approved
0.7105	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7750	Discontinued
0.7093	Intermediate Similarity	NPD7524	Approved
0.7065	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD4697	Phase 3
0.7033	Intermediate Similarity	NPD5221	Approved
0.7033	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5222	Approved
0.6989	Remote Similarity	NPD4696	Approved
0.6989	Remote Similarity	NPD7639	Approved
0.6989	Remote Similarity	NPD5286	Approved
0.6989	Remote Similarity	NPD5285	Approved
0.6989	Remote Similarity	NPD7640	Approved
0.6989	Remote Similarity	NPD4700	Approved
0.6988	Remote Similarity	NPD6902	Approved
0.6957	Remote Similarity	NPD5173	Approved
0.6957	Remote Similarity	NPD7902	Approved
0.6941	Remote Similarity	NPD3668	Phase 3
0.6932	Remote Similarity	NPD4753	Phase 2
0.6915	Remote Similarity	NPD5223	Approved
0.6905	Remote Similarity	NPD4221	Approved
0.6905	Remote Similarity	NPD4223	Phase 3
0.6889	Remote Similarity	NPD6399	Phase 3
0.6882	Remote Similarity	NPD5290	Discontinued
0.686	Remote Similarity	NPD5329	Approved
0.6842	Remote Similarity	NPD4633	Approved
0.6842	Remote Similarity	NPD5226	Approved
0.6842	Remote Similarity	NPD5211	Phase 2
0.6842	Remote Similarity	NPD5224	Approved
0.6842	Remote Similarity	NPD5225	Approved
0.6824	Remote Similarity	NPD4788	Approved
0.6804	Remote Similarity	NPD6675	Approved
0.6804	Remote Similarity	NPD5739	Approved
0.6804	Remote Similarity	NPD6402	Approved
0.6804	Remote Similarity	NPD7128	Approved
0.6795	Remote Similarity	NPD4787	Phase 1
0.6782	Remote Similarity	NPD5279	Phase 3
0.6782	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7087	Discontinued
0.6771	Remote Similarity	NPD5175	Approved
0.6771	Remote Similarity	NPD4754	Approved
0.6771	Remote Similarity	NPD5174	Approved
0.6744	Remote Similarity	NPD4197	Approved
0.6714	Remote Similarity	NPD342	Phase 1
0.6702	Remote Similarity	NPD4225	Approved
0.6701	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6633	Remote Similarity	NPD4768	Approved
0.6633	Remote Similarity	NPD4767	Approved
0.663	Remote Similarity	NPD7900	Approved
0.663	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6373	Approved
0.66	Remote Similarity	NPD6372	Approved
0.6596	Remote Similarity	NPD6083	Phase 2
0.6596	Remote Similarity	NPD6084	Phase 2
0.6593	Remote Similarity	NPD8035	Phase 2
0.6593	Remote Similarity	NPD8034	Phase 2
0.6591	Remote Similarity	NPD7334	Approved
0.6591	Remote Similarity	NPD4623	Approved
0.6591	Remote Similarity	NPD4690	Approved
0.6591	Remote Similarity	NPD6409	Approved
0.6591	Remote Similarity	NPD4688	Approved
0.6591	Remote Similarity	NPD5330	Approved
0.6591	Remote Similarity	NPD5205	Approved
0.6591	Remote Similarity	NPD4138	Approved
0.6591	Remote Similarity	NPD4689	Approved
0.6591	Remote Similarity	NPD6684	Approved
0.6591	Remote Similarity	NPD7146	Approved
0.6591	Remote Similarity	NPD4693	Phase 3
0.6591	Remote Similarity	NPD4519	Discontinued
0.6591	Remote Similarity	NPD7521	Approved
0.6566	Remote Similarity	NPD5701	Approved
0.6566	Remote Similarity	NPD5697	Approved
0.6559	Remote Similarity	NPD5210	Approved
0.6559	Remote Similarity	NPD4629	Approved
0.6556	Remote Similarity	NPD6051	Approved
0.6535	Remote Similarity	NPD6883	Approved
0.6535	Remote Similarity	NPD7102	Approved
0.6535	Remote Similarity	NPD7290	Approved
0.6517	Remote Similarity	NPD3573	Approved
0.6515	Remote Similarity	NPD385	Approved
0.6515	Remote Similarity	NPD384	Approved
0.65	Remote Similarity	NPD4729	Approved
0.65	Remote Similarity	NPD5128	Approved
0.65	Remote Similarity	NPD6011	Approved
0.65	Remote Similarity	NPD4730	Approved
0.65	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6650	Approved
0.6471	Remote Similarity	NPD6847	Approved
0.6471	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD6869	Approved
0.6471	Remote Similarity	NPD6617	Approved
0.6471	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8130	Phase 1
0.6456	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4723	Approved
0.6444	Remote Similarity	NPD6903	Approved
0.6444	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4722	Approved
0.6436	Remote Similarity	NPD6014	Approved
0.6436	Remote Similarity	NPD6012	Approved
0.6436	Remote Similarity	NPD6013	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6413	Remote Similarity	NPD6411	Approved
0.6408	Remote Similarity	NPD8297	Approved
0.6408	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD5690	Phase 2
0.6404	Remote Similarity	NPD4694	Approved
0.6404	Remote Similarity	NPD5280	Approved
0.6392	Remote Similarity	NPD4159	Approved
0.6386	Remote Similarity	NPD6117	Approved
0.6373	Remote Similarity	NPD5250	Approved
0.6373	Remote Similarity	NPD5169	Approved
0.6373	Remote Similarity	NPD5247	Approved
0.6373	Remote Similarity	NPD5251	Approved
0.6373	Remote Similarity	NPD5248	Approved
0.6373	Remote Similarity	NPD4634	Approved
0.6373	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5249	Phase 3
0.6373	Remote Similarity	NPD5135	Approved
0.6341	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5168	Approved
0.6327	Remote Similarity	NPD7632	Discontinued
0.6311	Remote Similarity	NPD5215	Approved
0.6311	Remote Similarity	NPD5216	Approved
0.6311	Remote Similarity	NPD5127	Approved
0.6311	Remote Similarity	NPD5217	Approved
0.631	Remote Similarity	NPD6116	Phase 1
0.6304	Remote Similarity	NPD7136	Phase 2
0.6292	Remote Similarity	NPD1696	Phase 3
0.6265	Remote Similarity	NPD3703	Phase 2
0.6264	Remote Similarity	NPD6672	Approved
0.6264	Remote Similarity	NPD5737	Approved
0.6237	Remote Similarity	NPD7637	Suspended
0.6235	Remote Similarity	NPD6118	Approved
0.6235	Remote Similarity	NPD6697	Approved
0.6235	Remote Similarity	NPD6115	Approved
0.6235	Remote Similarity	NPD6114	Approved
0.6222	Remote Similarity	NPD6098	Approved
0.622	Remote Similarity	NPD4732	Discontinued

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