NPASS Compound

Structure

NPC34834 OpenBabel07101718282D 22 23 0 0 1 0 0 0 0 0999 V2000 2.5981 0.5000 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 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 -0.8660 0.5000 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 0.8660 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 1.7321 3.0000 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 -0.0000 -1.0000 0.0000 C 0 0 1 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 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 1 0 0 0 17 22 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	349.671
LogP:	4.141
LogD:	3.62
LogS:	-4.188
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	4.377
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:	-4.37
MDCK Permeability:	2.3391374270431697e-05
Pgp-inhibitor:	0.493
Pgp-substrate:	0.284
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	92.97813415527344%
Volume Distribution (VD):	1.138
Pgp-substrate:	4.0350446701049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.198
CYP2C9-substrate:	0.655
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.608
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	8.49
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.265
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.933
Carcinogencity:	0.044
Eye Corrosion:	0.603
Eye Irritation:	0.919
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC34834

Natural Product ID:	NPC34834
*Common Name:**	Physacoztomatin
IUPAC Name:	(E,4R)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-ene-1,4-diol
Synonyms:	Physacoztomatin
Standard InCHIKey:	LHUGFIFIFQNHDA-BVTYEUJZSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-14-7-8-18-19(3,4)10-6-11-20(18,5)16(14)13-17(22)15(2)9-12-21/h7,9,16-18,21-22H,6,8,10-13H2,1-5H3/b15-9+/t16-,17+,18-,20+/m0/s1
SMILES:	OC/C=C(/[C@@H](C[C@H]1C(=CC[C@@H]2[C@]1(C)CCCC2(C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172818
PubChem CID:	49799161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO23525	Physalis sordida	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20575572]
NPO23525	Physalis sordida	Species	Solanaceae	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	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	65.8	%	PMID[496301]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	490.0	nM	PMID[496301]

☑ 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 NPC34834 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	151
0.1-0.2	1291
0.2-0.3	6466
0.3-0.4	16066
0.4-0.5	8540
0.5-0.6	6010
0.6-0.7	3143
0.7-0.8	843
0.8-0.85	135
0.85-0.9	38
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9254	High Similarity	NPC474248
0.9254	High Similarity	NPC471560
0.9242	High Similarity	NPC114651
0.9242	High Similarity	NPC68703
0.9242	High Similarity	NPC69649
0.9155	High Similarity	NPC91594
0.9104	High Similarity	NPC208999
0.9104	High Similarity	NPC96484
0.9091	High Similarity	NPC202017
0.9028	High Similarity	NPC83351
0.9028	High Similarity	NPC167891
0.9014	High Similarity	NPC247325
0.9014	High Similarity	NPC265588
0.9014	High Similarity	NPC244488
0.9	High Similarity	NPC306727
0.9	High Similarity	NPC476366
0.9	High Similarity	NPC201048
0.8955	High Similarity	NPC171225
0.8904	High Similarity	NPC81306
0.8904	High Similarity	NPC28862
0.8904	High Similarity	NPC143182
0.8904	High Similarity	NPC47982
0.8904	High Similarity	NPC30986
0.8904	High Similarity	NPC209430
0.8904	High Similarity	NPC84694
0.8904	High Similarity	NPC109546
0.8889	High Similarity	NPC470711
0.8889	High Similarity	NPC470758
0.8873	High Similarity	NPC32832
0.8857	High Similarity	NPC474140
0.8857	High Similarity	NPC130665
0.8857	High Similarity	NPC471799
0.8806	High Similarity	NPC279434
0.8788	High Similarity	NPC323424
0.8788	High Similarity	NPC96793
0.8784	High Similarity	NPC295131
0.8784	High Similarity	NPC234193
0.8767	High Similarity	NPC476314
0.8767	High Similarity	NPC474216
0.875	High Similarity	NPC253190
0.875	High Similarity	NPC470749
0.8732	High Similarity	NPC471797
0.8714	High Similarity	NPC242001
0.8714	High Similarity	NPC23954
0.8714	High Similarity	NPC167706
0.8676	High Similarity	NPC197805
0.8667	High Similarity	NPC476646
0.8667	High Similarity	NPC264245
0.8667	High Similarity	NPC209620
0.8667	High Similarity	NPC23852
0.8649	High Similarity	NPC242767
0.8592	High Similarity	NPC265485
0.8592	High Similarity	NPC182717
0.8592	High Similarity	NPC474743
0.8592	High Similarity	NPC220939
0.8571	High Similarity	NPC92801
0.8571	High Similarity	NPC145498
0.8553	High Similarity	NPC50964
0.8553	High Similarity	NPC202389
0.8553	High Similarity	NPC87489
0.8553	High Similarity	NPC101462
0.8553	High Similarity	NPC189972
0.8553	High Similarity	NPC49964
0.8551	High Similarity	NPC471238
0.8551	High Similarity	NPC216460
0.8533	High Similarity	NPC96362
0.8533	High Similarity	NPC164840
0.8533	High Similarity	NPC241290
0.8533	High Similarity	NPC209944
0.8529	High Similarity	NPC476039
0.8529	High Similarity	NPC286669
0.8529	High Similarity	NPC476406
0.8529	High Similarity	NPC222366
0.8514	High Similarity	NPC477514
0.8514	High Similarity	NPC11908
0.8514	High Similarity	NPC473943
0.8507	High Similarity	NPC290367
0.8507	High Similarity	NPC107540
0.8507	High Similarity	NPC225415
0.8493	Intermediate Similarity	NPC321381
0.8493	Intermediate Similarity	NPC321016
0.8493	Intermediate Similarity	NPC107059
0.8472	Intermediate Similarity	NPC469534
0.8472	Intermediate Similarity	NPC469593
0.8472	Intermediate Similarity	NPC100334
0.8472	Intermediate Similarity	NPC91858
0.8472	Intermediate Similarity	NPC477138
0.8472	Intermediate Similarity	NPC243342
0.8472	Intermediate Similarity	NPC469533
0.8451	Intermediate Similarity	NPC110799
0.8451	Intermediate Similarity	NPC477792
0.8451	Intermediate Similarity	NPC164022
0.8442	Intermediate Similarity	NPC475789
0.8442	Intermediate Similarity	NPC474634
0.8442	Intermediate Similarity	NPC470384
0.8442	Intermediate Similarity	NPC317458
0.8429	Intermediate Similarity	NPC9942
0.8429	Intermediate Similarity	NPC473893
0.8421	Intermediate Similarity	NPC474752
0.8421	Intermediate Similarity	NPC7505
0.8421	Intermediate Similarity	NPC474683
0.8421	Intermediate Similarity	NPC474731
0.8421	Intermediate Similarity	NPC82986
0.8421	Intermediate Similarity	NPC249423
0.8421	Intermediate Similarity	NPC47761
0.8421	Intermediate Similarity	NPC474759
0.8382	Intermediate Similarity	NPC163678
0.8378	Intermediate Similarity	NPC318495
0.8378	Intermediate Similarity	NPC157996
0.8378	Intermediate Similarity	NPC40394
0.8378	Intermediate Similarity	NPC101475
0.8378	Intermediate Similarity	NPC155986
0.8378	Intermediate Similarity	NPC34177
0.8378	Intermediate Similarity	NPC198968
0.8378	Intermediate Similarity	NPC74995
0.8378	Intermediate Similarity	NPC471798
0.8378	Intermediate Similarity	NPC130136
0.8378	Intermediate Similarity	NPC214570
0.8378	Intermediate Similarity	NPC472805
0.8378	Intermediate Similarity	NPC90979
0.8358	Intermediate Similarity	NPC174956
0.8358	Intermediate Similarity	NPC81615
0.8356	Intermediate Similarity	NPC257347
0.8356	Intermediate Similarity	NPC171148
0.8356	Intermediate Similarity	NPC230301
0.8356	Intermediate Similarity	NPC304309
0.8356	Intermediate Similarity	NPC288035
0.8356	Intermediate Similarity	NPC69383
0.8356	Intermediate Similarity	NPC133580
0.8356	Intermediate Similarity	NPC162742
0.8356	Intermediate Similarity	NPC66566
0.8356	Intermediate Similarity	NPC22105
0.8356	Intermediate Similarity	NPC136188
0.8356	Intermediate Similarity	NPC134847
0.8356	Intermediate Similarity	NPC285893
0.8356	Intermediate Similarity	NPC313179
0.8356	Intermediate Similarity	NPC141071
0.8356	Intermediate Similarity	NPC28657
0.8356	Intermediate Similarity	NPC291503
0.8356	Intermediate Similarity	NPC471723
0.8356	Intermediate Similarity	NPC477923
0.8333	Intermediate Similarity	NPC474047
0.8333	Intermediate Similarity	NPC66020
0.8333	Intermediate Similarity	NPC231310
0.8333	Intermediate Similarity	NPC238485
0.8333	Intermediate Similarity	NPC185568
0.8333	Intermediate Similarity	NPC205845
0.8333	Intermediate Similarity	NPC68443
0.8312	Intermediate Similarity	NPC470049
0.8312	Intermediate Similarity	NPC304285
0.8312	Intermediate Similarity	NPC296701
0.8312	Intermediate Similarity	NPC155521
0.8312	Intermediate Similarity	NPC218616
0.831	Intermediate Similarity	NPC189745
0.8289	Intermediate Similarity	NPC281880
0.8286	Intermediate Similarity	NPC160209
0.8286	Intermediate Similarity	NPC32055
0.8267	Intermediate Similarity	NPC158662
0.8267	Intermediate Similarity	NPC477522
0.8267	Intermediate Similarity	NPC300499
0.8267	Intermediate Similarity	NPC297996
0.8267	Intermediate Similarity	NPC98386
0.8267	Intermediate Similarity	NPC87604
0.8267	Intermediate Similarity	NPC470396
0.8267	Intermediate Similarity	NPC99168
0.8267	Intermediate Similarity	NPC253807
0.8267	Intermediate Similarity	NPC22955
0.8267	Intermediate Similarity	NPC230295
0.8267	Intermediate Similarity	NPC196753
0.8267	Intermediate Similarity	NPC275910
0.8267	Intermediate Similarity	NPC474989
0.8261	Intermediate Similarity	NPC149680
0.8243	Intermediate Similarity	NPC189883
0.8243	Intermediate Similarity	NPC96319
0.8243	Intermediate Similarity	NPC120098
0.8243	Intermediate Similarity	NPC46160
0.8243	Intermediate Similarity	NPC274079
0.8243	Intermediate Similarity	NPC30590
0.8243	Intermediate Similarity	NPC477925
0.8243	Intermediate Similarity	NPC290598
0.8243	Intermediate Similarity	NPC73875
0.8243	Intermediate Similarity	NPC122418
0.8243	Intermediate Similarity	NPC265328
0.8243	Intermediate Similarity	NPC300324
0.8243	Intermediate Similarity	NPC240604
0.8243	Intermediate Similarity	NPC106364
0.8243	Intermediate Similarity	NPC113733
0.8243	Intermediate Similarity	NPC202642
0.8243	Intermediate Similarity	NPC129165
0.8243	Intermediate Similarity	NPC134330
0.8243	Intermediate Similarity	NPC470362
0.8243	Intermediate Similarity	NPC106432
0.8243	Intermediate Similarity	NPC27765
0.8235	Intermediate Similarity	NPC68656
0.8235	Intermediate Similarity	NPC309300
0.8228	Intermediate Similarity	NPC471224
0.8228	Intermediate Similarity	NPC474083
0.8228	Intermediate Similarity	NPC274448
0.8228	Intermediate Similarity	NPC274724
0.8228	Intermediate Similarity	NPC109528

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 NPC34834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1761
0.2-0.3	4048
0.3-0.4	2236
0.4-0.5	588
0.5-0.6	250
0.6-0.7	86
0.7-0.8	40
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8356	Intermediate Similarity	NPD7339	Approved
0.8356	Intermediate Similarity	NPD6942	Approved
0.8356	Intermediate Similarity	NPD8264	Approved
0.8243	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7645	Phase 2
0.7973	Intermediate Similarity	NPD6924	Approved
0.7973	Intermediate Similarity	NPD6926	Approved
0.7941	Intermediate Similarity	NPD368	Approved
0.7922	Intermediate Similarity	NPD6929	Approved
0.7846	Intermediate Similarity	NPD342	Phase 1
0.7821	Intermediate Similarity	NPD6931	Approved
0.7821	Intermediate Similarity	NPD6930	Phase 2
0.7821	Intermediate Similarity	NPD7525	Registered
0.7805	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6933	Approved
0.7703	Intermediate Similarity	NPD4243	Approved
0.7671	Intermediate Similarity	NPD6922	Approved
0.7671	Intermediate Similarity	NPD6923	Approved
0.7662	Intermediate Similarity	NPD6925	Approved
0.7662	Intermediate Similarity	NPD5776	Phase 2
0.7654	Intermediate Similarity	NPD4786	Approved
0.7625	Intermediate Similarity	NPD3667	Approved
0.7595	Intermediate Similarity	NPD7514	Phase 3
0.7595	Intermediate Similarity	NPD7332	Phase 2
0.7568	Intermediate Similarity	NPD7143	Approved
0.7568	Intermediate Similarity	NPD7144	Approved
0.7564	Intermediate Similarity	NPD7145	Approved
0.7531	Intermediate Similarity	NPD6695	Phase 3
0.75	Intermediate Similarity	NPD6902	Approved
0.75	Intermediate Similarity	NPD4785	Approved
0.75	Intermediate Similarity	NPD4784	Approved
0.7467	Intermediate Similarity	NPD7151	Approved
0.7467	Intermediate Similarity	NPD7150	Approved
0.7467	Intermediate Similarity	NPD7152	Approved
0.7439	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3665	Phase 1
0.7439	Intermediate Similarity	NPD3666	Approved
0.7439	Intermediate Similarity	NPD3133	Approved
0.7375	Intermediate Similarity	NPD7509	Discontinued
0.7349	Intermediate Similarity	NPD6893	Approved
0.7284	Intermediate Similarity	NPD6898	Phase 1
0.7262	Intermediate Similarity	NPD3618	Phase 1
0.7215	Intermediate Similarity	NPD6932	Approved
0.7209	Intermediate Similarity	NPD5328	Approved
0.7206	Intermediate Similarity	NPD4219	Approved
0.7179	Intermediate Similarity	NPD5275	Approved
0.7179	Intermediate Similarity	NPD4190	Phase 3
0.7176	Intermediate Similarity	NPD7750	Discontinued
0.7176	Intermediate Similarity	NPD7524	Approved
0.716	Intermediate Similarity	NPD4748	Discontinued
0.7059	Intermediate Similarity	NPD5279	Phase 3
0.7059	Intermediate Similarity	NPD4519	Discontinued
0.7059	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD7515	Phase 2
0.7045	Intermediate Similarity	NPD6079	Approved
0.7037	Intermediate Similarity	NPD6683	Phase 2
0.7037	Intermediate Similarity	NPD4195	Approved
0.6882	Remote Similarity	NPD7640	Approved
0.6882	Remote Similarity	NPD7639	Approved
0.6854	Remote Similarity	NPD7087	Discontinued
0.6824	Remote Similarity	NPD3668	Phase 3
0.6818	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD6051	Approved
0.6786	Remote Similarity	NPD4223	Phase 3
0.6786	Remote Similarity	NPD4221	Approved
0.6778	Remote Similarity	NPD6399	Phase 3
0.6778	Remote Similarity	NPD4202	Approved
0.6774	Remote Similarity	NPD7638	Approved
0.6747	Remote Similarity	NPD4695	Discontinued
0.6744	Remote Similarity	NPD5329	Approved
0.6709	Remote Similarity	NPD4732	Discontinued
0.6707	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6628	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4197	Approved
0.6596	Remote Similarity	NPD4225	Approved
0.6593	Remote Similarity	NPD5778	Approved
0.6593	Remote Similarity	NPD5779	Approved
0.6562	Remote Similarity	NPD5211	Phase 2
0.6559	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5222	Approved
0.6559	Remote Similarity	NPD4697	Phase 3
0.6559	Remote Similarity	NPD5221	Approved
0.6556	Remote Similarity	NPD7136	Phase 2
0.6552	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1696	Phase 3
0.6517	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6903	Approved
0.6512	Remote Similarity	NPD4788	Approved
0.6506	Remote Similarity	NPD3617	Approved
0.6489	Remote Similarity	NPD5173	Approved
0.6489	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD6084	Phase 2
0.6489	Remote Similarity	NPD6083	Phase 2
0.6489	Remote Similarity	NPD7902	Approved
0.6484	Remote Similarity	NPD6411	Approved
0.6477	Remote Similarity	NPD4689	Approved
0.6477	Remote Similarity	NPD5205	Approved
0.6477	Remote Similarity	NPD5280	Approved
0.6477	Remote Similarity	NPD4690	Approved
0.6477	Remote Similarity	NPD4688	Approved
0.6477	Remote Similarity	NPD4694	Approved
0.6477	Remote Similarity	NPD5690	Phase 2
0.6477	Remote Similarity	NPD4693	Phase 3
0.6477	Remote Similarity	NPD4138	Approved
0.6462	Remote Similarity	NPD4265	Approved
0.6452	Remote Similarity	NPD4629	Approved
0.6452	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD5141	Approved
0.6421	Remote Similarity	NPD5290	Discontinued
0.6395	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4700	Approved
0.6354	Remote Similarity	NPD5286	Approved
0.6354	Remote Similarity	NPD5285	Approved
0.6354	Remote Similarity	NPD4696	Approved
0.6353	Remote Similarity	NPD4820	Approved
0.6353	Remote Similarity	NPD4822	Approved
0.6353	Remote Similarity	NPD4819	Approved
0.6353	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4821	Approved
0.6333	Remote Similarity	NPD4723	Approved
0.6333	Remote Similarity	NPD6672	Approved
0.6333	Remote Similarity	NPD4722	Approved
0.6333	Remote Similarity	NPD5737	Approved
0.6322	Remote Similarity	NPD5362	Discontinued
0.6322	Remote Similarity	NPD5332	Approved
0.6322	Remote Similarity	NPD5331	Approved
0.631	Remote Similarity	NPD4271	Approved
0.631	Remote Similarity	NPD4268	Approved
0.6292	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5223	Approved
0.6279	Remote Similarity	NPD4790	Discontinued
0.6279	Remote Similarity	NPD4692	Approved
0.6279	Remote Similarity	NPD4139	Approved
0.6277	Remote Similarity	NPD5695	Phase 3
0.6267	Remote Similarity	NPD4193	Approved
0.6267	Remote Similarity	NPD4191	Approved
0.6267	Remote Similarity	NPD4192	Approved
0.6267	Remote Similarity	NPD4194	Approved
0.6264	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6101	Approved
0.6264	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5224	Approved
0.6224	Remote Similarity	NPD7632	Discontinued
0.6224	Remote Similarity	NPD5226	Approved
0.6224	Remote Similarity	NPD5225	Approved
0.6224	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD4269	Approved
0.6207	Remote Similarity	NPD4270	Approved
0.62	Remote Similarity	NPD5739	Approved
0.62	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD6675	Approved
0.62	Remote Similarity	NPD7128	Approved
0.6186	Remote Similarity	NPD6404	Discontinued
0.618	Remote Similarity	NPD1694	Approved
0.617	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7900	Approved
0.6163	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5175	Approved
0.6162	Remote Similarity	NPD5174	Approved
0.6162	Remote Similarity	NPD4754	Approved
0.6154	Remote Similarity	NPD7331	Phase 2
0.6145	Remote Similarity	NPD8039	Approved
0.6139	Remote Similarity	NPD6412	Phase 2
0.6136	Remote Similarity	NPD7154	Phase 3
0.6129	Remote Similarity	NPD5281	Approved
0.6129	Remote Similarity	NPD5284	Approved
0.6125	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4137	Phase 3
0.6122	Remote Similarity	NPD4159	Approved
0.6119	Remote Similarity	NPD384	Approved
0.6119	Remote Similarity	NPD385	Approved
0.6111	Remote Similarity	NPD6098	Approved
0.6104	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5696	Approved
0.6078	Remote Similarity	NPD6686	Approved
0.6078	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD6881	Approved
0.6075	Remote Similarity	NPD7115	Discovery
0.6071	Remote Similarity	NPD1346	Approved
0.6049	Remote Similarity	NPD4787	Phase 1
0.6049	Remote Similarity	NPD4245	Approved
0.6049	Remote Similarity	NPD4747	Approved
0.6049	Remote Similarity	NPD4244	Approved
0.6049	Remote Similarity	NPD4691	Approved
0.604	Remote Similarity	NPD4767	Approved
0.604	Remote Similarity	NPD4768	Approved
0.604	Remote Similarity	NPD6640	Phase 3
0.6026	Remote Similarity	NPD7341	Phase 2
0.6026	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5733	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