NPASS Compound

Structure

NPC68703 OpenBabel07101719522D 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 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 -1.7321 2.0000 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 -0.8660 -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 -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 -0.8660 4.5000 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 -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 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 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 17 20 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	349.671
LogP:	3.53
LogD:	3.477
LogS:	-2.899
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	4.136
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.468
MDCK Permeability:	1.3098421732138377e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.754

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.61
Plasma Protein Binding (PPB):	44.60325241088867%
Volume Distribution (VD):	0.964
Pgp-substrate:	54.534236907958984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.43
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.602
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	7.496
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.677
Maximum Recommended Daily Dose:	0.52
Skin Sensitization:	0.897
Carcinogencity:	0.675
Eye Corrosion:	0.102
Eye Irritation:	0.622
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC68703

Natural Product ID:	NPC68703
*Common Name:**	(+)-(Z)-Labda-8(17),13-Diene-15,16-Diol
IUPAC Name:	(Z)-2-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]but-2-ene-1,4-diol
Synonyms:
Standard InCHIKey:	WJPNUXZXCGQJQX-JRPFFITISA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-15-6-9-18-19(2,3)11-5-12-20(18,4)17(15)8-7-16(14-22)10-13-21/h10,17-18,21-22H,1,5-9,11-14H2,2-4H3/b16-10-/t17-,18-,20+/m0/s1
SMILES:	OC/C=C(/CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3421653
PubChem CID:	11415540
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
NPO7052	Physalis nicandroides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25634541]
NPO7052	Physalis nicandroides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31429569]
NPO7052	Physalis nicandroides	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
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	33.9	%	PMID[508232]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	41.35	%	PMID[508231]

☑ 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 NPC68703 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	149
0.1-0.2	1369
0.2-0.3	6824
0.3-0.4	16403
0.4-0.5	8430
0.5-0.6	5904
0.6-0.7	2725
0.7-0.8	753
0.8-0.85	101
0.85-0.9	27
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC69649
0.9242	High Similarity	NPC34834
0.9118	High Similarity	NPC476366
0.9118	High Similarity	NPC306727
0.9118	High Similarity	NPC201048
0.8986	High Similarity	NPC32832
0.8971	High Similarity	NPC474743
0.8923	High Similarity	NPC476406
0.8923	High Similarity	NPC149680
0.8857	High Similarity	NPC470749
0.8788	High Similarity	NPC171225
0.8788	High Similarity	NPC197805
0.8732	High Similarity	NPC470758
0.8732	High Similarity	NPC91594
0.8732	High Similarity	NPC470711
0.8657	High Similarity	NPC160209
0.8636	High Similarity	NPC222366
0.8636	High Similarity	NPC476039
0.8636	High Similarity	NPC286669
0.8611	High Similarity	NPC239098
0.8611	High Similarity	NPC167891
0.8611	High Similarity	NPC476314
0.8611	High Similarity	NPC83351
0.8592	High Similarity	NPC244488
0.8592	High Similarity	NPC253190
0.8592	High Similarity	NPC247325
0.8551	High Similarity	NPC242001
0.8551	High Similarity	NPC167706
0.8548	High Similarity	NPC11130
0.8529	High Similarity	NPC474248
0.8529	High Similarity	NPC471560
0.8529	High Similarity	NPC9942
0.8507	High Similarity	NPC114651
0.8493	Intermediate Similarity	NPC209430
0.8493	Intermediate Similarity	NPC28862
0.8493	Intermediate Similarity	NPC109546
0.8493	Intermediate Similarity	NPC81306
0.8493	Intermediate Similarity	NPC30986
0.8493	Intermediate Similarity	NPC84694
0.8493	Intermediate Similarity	NPC47982
0.8493	Intermediate Similarity	NPC143182
0.8429	Intermediate Similarity	NPC68443
0.8429	Intermediate Similarity	NPC471799
0.8406	Intermediate Similarity	NPC145498
0.8406	Intermediate Similarity	NPC189745
0.8382	Intermediate Similarity	NPC32055
0.8382	Intermediate Similarity	NPC96484
0.8382	Intermediate Similarity	NPC208999
0.8382	Intermediate Similarity	NPC471238
0.8382	Intermediate Similarity	NPC216460
0.8378	Intermediate Similarity	NPC234193
0.8378	Intermediate Similarity	NPC281880
0.8378	Intermediate Similarity	NPC295131
0.8378	Intermediate Similarity	NPC96362
0.8358	Intermediate Similarity	NPC202017
0.8358	Intermediate Similarity	NPC279434
0.8356	Intermediate Similarity	NPC474216
0.8356	Intermediate Similarity	NPC11908
0.8333	Intermediate Similarity	NPC107540
0.8333	Intermediate Similarity	NPC225415
0.8333	Intermediate Similarity	NPC265588
0.831	Intermediate Similarity	NPC243342
0.831	Intermediate Similarity	NPC471797
0.831	Intermediate Similarity	NPC477138
0.831	Intermediate Similarity	NPC469534
0.831	Intermediate Similarity	NPC469593
0.831	Intermediate Similarity	NPC469533
0.831	Intermediate Similarity	NPC91858
0.8308	Intermediate Similarity	NPC41160
0.8286	Intermediate Similarity	NPC477792
0.8267	Intermediate Similarity	NPC23852
0.8267	Intermediate Similarity	NPC249423
0.8267	Intermediate Similarity	NPC159148
0.8267	Intermediate Similarity	NPC476646
0.8267	Intermediate Similarity	NPC209620
0.8267	Intermediate Similarity	NPC264245
0.8261	Intermediate Similarity	NPC473893
0.8209	Intermediate Similarity	NPC258595
0.8209	Intermediate Similarity	NPC163678
0.8194	Intermediate Similarity	NPC291503
0.8194	Intermediate Similarity	NPC66566
0.8194	Intermediate Similarity	NPC477923
0.8182	Intermediate Similarity	NPC81615
0.8169	Intermediate Similarity	NPC182717
0.8169	Intermediate Similarity	NPC474140
0.8169	Intermediate Similarity	NPC130665
0.8158	Intermediate Similarity	NPC2524
0.8158	Intermediate Similarity	NPC101462
0.8158	Intermediate Similarity	NPC296701
0.8158	Intermediate Similarity	NPC50964
0.8158	Intermediate Similarity	NPC155521
0.8158	Intermediate Similarity	NPC49964
0.8158	Intermediate Similarity	NPC189972
0.8158	Intermediate Similarity	NPC218616
0.8133	Intermediate Similarity	NPC164840
0.8133	Intermediate Similarity	NPC241290
0.8133	Intermediate Similarity	NPC209944
0.8108	Intermediate Similarity	NPC473943
0.8108	Intermediate Similarity	NPC297996
0.8108	Intermediate Similarity	NPC477514
0.8082	Intermediate Similarity	NPC477925
0.8082	Intermediate Similarity	NPC107059
0.8082	Intermediate Similarity	NPC274079
0.8082	Intermediate Similarity	NPC321381
0.8082	Intermediate Similarity	NPC321016
0.806	Intermediate Similarity	NPC96793
0.806	Intermediate Similarity	NPC309300
0.806	Intermediate Similarity	NPC68656
0.806	Intermediate Similarity	NPC290367
0.806	Intermediate Similarity	NPC323424
0.8056	Intermediate Similarity	NPC329090
0.8056	Intermediate Similarity	NPC100334
0.8056	Intermediate Similarity	NPC27395
0.8052	Intermediate Similarity	NPC474634
0.8052	Intermediate Similarity	NPC317458
0.8052	Intermediate Similarity	NPC475789
0.8028	Intermediate Similarity	NPC23954
0.8028	Intermediate Similarity	NPC471271
0.8028	Intermediate Similarity	NPC471268
0.8028	Intermediate Similarity	NPC471272
0.8026	Intermediate Similarity	NPC47761
0.8026	Intermediate Similarity	NPC474752
0.8026	Intermediate Similarity	NPC474759
0.8026	Intermediate Similarity	NPC7505
0.8026	Intermediate Similarity	NPC82986
0.8026	Intermediate Similarity	NPC474683
0.8026	Intermediate Similarity	NPC474731
0.8	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC122239
0.7973	Intermediate Similarity	NPC155986
0.7973	Intermediate Similarity	NPC318495
0.7973	Intermediate Similarity	NPC34177
0.7973	Intermediate Similarity	NPC471798
0.7973	Intermediate Similarity	NPC198968
0.7973	Intermediate Similarity	NPC40394
0.7973	Intermediate Similarity	NPC157996
0.7973	Intermediate Similarity	NPC472805
0.7973	Intermediate Similarity	NPC74995
0.7973	Intermediate Similarity	NPC101475
0.7973	Intermediate Similarity	NPC90979
0.7973	Intermediate Similarity	NPC477924
0.7973	Intermediate Similarity	NPC132542
0.7973	Intermediate Similarity	NPC130136
0.7949	Intermediate Similarity	NPC185568
0.7949	Intermediate Similarity	NPC476412
0.7949	Intermediate Similarity	NPC205845
0.7949	Intermediate Similarity	NPC102048
0.7949	Intermediate Similarity	NPC474047
0.7945	Intermediate Similarity	NPC141071
0.7945	Intermediate Similarity	NPC134847
0.7945	Intermediate Similarity	NPC230301
0.7945	Intermediate Similarity	NPC136188
0.7945	Intermediate Similarity	NPC133580
0.7945	Intermediate Similarity	NPC22105
0.7945	Intermediate Similarity	NPC288035
0.7945	Intermediate Similarity	NPC328104
0.7945	Intermediate Similarity	NPC471723
0.7945	Intermediate Similarity	NPC285893
0.7945	Intermediate Similarity	NPC162742
0.7945	Intermediate Similarity	NPC69383
0.7945	Intermediate Similarity	NPC319090
0.7945	Intermediate Similarity	NPC28657
0.7945	Intermediate Similarity	NPC257347
0.7945	Intermediate Similarity	NPC313179
0.7945	Intermediate Similarity	NPC171148
0.7945	Intermediate Similarity	NPC304309
0.7941	Intermediate Similarity	NPC27243
0.7941	Intermediate Similarity	NPC19569
0.7941	Intermediate Similarity	NPC476737
0.7922	Intermediate Similarity	NPC87489
0.7922	Intermediate Similarity	NPC304285
0.7922	Intermediate Similarity	NPC470049
0.7922	Intermediate Similarity	NPC202389
0.7917	Intermediate Similarity	NPC220939
0.7917	Intermediate Similarity	NPC265485
0.7917	Intermediate Similarity	NPC472506
0.791	Intermediate Similarity	NPC174956
0.7895	Intermediate Similarity	NPC306095
0.7895	Intermediate Similarity	NPC324772
0.7887	Intermediate Similarity	NPC92801
0.7879	Intermediate Similarity	NPC240506
0.7879	Intermediate Similarity	NPC66020
0.7867	Intermediate Similarity	NPC98386
0.7867	Intermediate Similarity	NPC87604
0.7867	Intermediate Similarity	NPC253807
0.7867	Intermediate Similarity	NPC474989
0.7867	Intermediate Similarity	NPC22955
0.7867	Intermediate Similarity	NPC167037
0.7867	Intermediate Similarity	NPC196753
0.7867	Intermediate Similarity	NPC158662
0.7867	Intermediate Similarity	NPC138621
0.7867	Intermediate Similarity	NPC285761
0.7867	Intermediate Similarity	NPC477522
0.7867	Intermediate Similarity	NPC470396
0.7867	Intermediate Similarity	NPC99168
0.7867	Intermediate Similarity	NPC300499
0.7867	Intermediate Similarity	NPC230295
0.7867	Intermediate Similarity	NPC244385
0.7867	Intermediate Similarity	NPC6978
0.7857	Intermediate Similarity	NPC94192

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 NPC68703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	1689
0.2-0.3	4142
0.3-0.4	2267
0.4-0.5	548
0.5-0.6	249
0.6-0.7	71
0.7-0.8	46
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
0.8056	Intermediate Similarity	NPD6924	Approved
0.8056	Intermediate Similarity	NPD6926	Approved
0.8	Intermediate Similarity	NPD6929	Approved
0.7945	Intermediate Similarity	NPD6942	Approved
0.7945	Intermediate Similarity	NPD7339	Approved
0.7945	Intermediate Similarity	NPD8264	Approved
0.7895	Intermediate Similarity	NPD6931	Approved
0.7895	Intermediate Similarity	NPD6930	Phase 2
0.7867	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6933	Approved
0.7763	Intermediate Similarity	NPD7645	Phase 2
0.7746	Intermediate Similarity	NPD6922	Approved
0.7746	Intermediate Similarity	NPD6923	Approved
0.7733	Intermediate Similarity	NPD6925	Approved
0.7733	Intermediate Similarity	NPD5776	Phase 2
0.7662	Intermediate Similarity	NPD7514	Phase 3
0.7662	Intermediate Similarity	NPD7332	Phase 2
0.7662	Intermediate Similarity	NPD7525	Registered
0.7656	Intermediate Similarity	NPD342	Phase 1
0.7639	Intermediate Similarity	NPD7144	Approved
0.7639	Intermediate Similarity	NPD7143	Approved
0.7632	Intermediate Similarity	NPD7145	Approved
0.7595	Intermediate Similarity	NPD6695	Phase 3
0.7564	Intermediate Similarity	NPD6902	Approved
0.7534	Intermediate Similarity	NPD7152	Approved
0.7534	Intermediate Similarity	NPD7150	Approved
0.7534	Intermediate Similarity	NPD4243	Approved
0.7534	Intermediate Similarity	NPD7151	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7509	Discontinued
0.7407	Intermediate Similarity	NPD6893	Approved
0.7342	Intermediate Similarity	NPD6898	Phase 1
0.7333	Intermediate Similarity	NPD4784	Approved
0.7333	Intermediate Similarity	NPD4785	Approved
0.7284	Intermediate Similarity	NPD4786	Approved
0.7273	Intermediate Similarity	NPD4219	Approved
0.7273	Intermediate Similarity	NPD6932	Approved
0.725	Intermediate Similarity	NPD3667	Approved
0.7246	Intermediate Similarity	NPD368	Approved
0.7229	Intermediate Similarity	NPD7524	Approved
0.7229	Intermediate Similarity	NPD7750	Discontinued
0.7089	Intermediate Similarity	NPD6683	Phase 2
0.7073	Intermediate Similarity	NPD3133	Approved
0.7073	Intermediate Similarity	NPD3665	Phase 1
0.7073	Intermediate Similarity	NPD3666	Approved
0.7013	Intermediate Similarity	NPD5275	Approved
0.7013	Intermediate Similarity	NPD4190	Phase 3
0.6905	Remote Similarity	NPD3618	Phase 1
0.6905	Remote Similarity	NPD4519	Discontinued
0.6905	Remote Similarity	NPD4623	Approved
0.6897	Remote Similarity	NPD7087	Discontinued
0.6875	Remote Similarity	NPD4195	Approved
0.686	Remote Similarity	NPD5328	Approved
0.6829	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4695	Discontinued
0.6774	Remote Similarity	NPD4265	Approved
0.6739	Remote Similarity	NPD7640	Approved
0.6739	Remote Similarity	NPD7639	Approved
0.6706	Remote Similarity	NPD5279	Phase 3
0.6705	Remote Similarity	NPD6079	Approved
0.6705	Remote Similarity	NPD7637	Suspended
0.6705	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD4753	Phase 2
0.663	Remote Similarity	NPD4225	Approved
0.663	Remote Similarity	NPD7638	Approved
0.6627	Remote Similarity	NPD4221	Approved
0.6627	Remote Similarity	NPD4223	Phase 3
0.6591	Remote Similarity	NPD7136	Phase 2
0.6588	Remote Similarity	NPD5329	Approved
0.6585	Remote Similarity	NPD4748	Discontinued
0.6548	Remote Similarity	NPD4788	Approved
0.6543	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4732	Discontinued
0.6477	Remote Similarity	NPD6051	Approved
0.6471	Remote Similarity	NPD4197	Approved
0.6471	Remote Similarity	NPD3668	Phase 3
0.6444	Remote Similarity	NPD4202	Approved
0.6444	Remote Similarity	NPD6399	Phase 3
0.6395	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7748	Approved
0.6344	Remote Similarity	NPD6083	Phase 2
0.6344	Remote Similarity	NPD6084	Phase 2
0.6341	Remote Similarity	NPD3617	Approved
0.6322	Remote Similarity	NPD7521	Approved
0.6322	Remote Similarity	NPD5330	Approved
0.6322	Remote Similarity	NPD4689	Approved
0.6322	Remote Similarity	NPD5205	Approved
0.6322	Remote Similarity	NPD7334	Approved
0.6322	Remote Similarity	NPD4688	Approved
0.6322	Remote Similarity	NPD7146	Approved
0.6322	Remote Similarity	NPD4138	Approved
0.6322	Remote Similarity	NPD6409	Approved
0.6322	Remote Similarity	NPD4690	Approved
0.6322	Remote Similarity	NPD4693	Phase 3
0.6322	Remote Similarity	NPD6684	Approved
0.6304	Remote Similarity	NPD4629	Approved
0.6304	Remote Similarity	NPD5210	Approved
0.6301	Remote Similarity	NPD4191	Approved
0.6301	Remote Similarity	NPD4194	Approved
0.6301	Remote Similarity	NPD4192	Approved
0.6301	Remote Similarity	NPD4193	Approved
0.6279	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5778	Approved
0.6264	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.6237	Remote Similarity	NPD5222	Approved
0.6237	Remote Similarity	NPD4697	Phase 3
0.6237	Remote Similarity	NPD5221	Approved
0.6237	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD1696	Phase 3
0.6196	Remote Similarity	NPD5771	Approved
0.619	Remote Similarity	NPD4819	Approved
0.619	Remote Similarity	NPD4820	Approved
0.619	Remote Similarity	NPD4822	Approved
0.619	Remote Similarity	NPD4821	Approved
0.618	Remote Similarity	NPD6903	Approved
0.618	Remote Similarity	NPD4723	Approved
0.618	Remote Similarity	NPD6672	Approved
0.618	Remote Similarity	NPD5737	Approved
0.618	Remote Similarity	NPD4722	Approved
0.618	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD8039	Approved
0.617	Remote Similarity	NPD7902	Approved
0.617	Remote Similarity	NPD4755	Approved
0.617	Remote Similarity	NPD5173	Approved
0.6163	Remote Similarity	NPD5331	Approved
0.6163	Remote Similarity	NPD5332	Approved
0.6163	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD6411	Approved
0.6145	Remote Similarity	NPD4271	Approved
0.6145	Remote Similarity	NPD4268	Approved
0.6136	Remote Similarity	NPD4694	Approved
0.6136	Remote Similarity	NPD5690	Phase 2
0.6136	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5280	Approved
0.6133	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5141	Approved
0.6118	Remote Similarity	NPD4790	Discontinued
0.6111	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5290	Discontinued
0.61	Remote Similarity	NPD6686	Approved
0.6098	Remote Similarity	NPD1346	Approved
0.6082	Remote Similarity	NPD7632	Discontinued
0.6061	Remote Similarity	NPD6640	Phase 3
0.6053	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4269	Approved
0.6047	Remote Similarity	NPD4270	Approved
0.6042	Remote Similarity	NPD6404	Discontinued
0.6042	Remote Similarity	NPD4700	Approved
0.6042	Remote Similarity	NPD4696	Approved
0.6042	Remote Similarity	NPD5285	Approved
0.6042	Remote Similarity	NPD5286	Approved
0.6026	Remote Similarity	NPD6705	Phase 1
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5223	Approved
0.5977	Remote Similarity	NPD7154	Phase 3
0.5974	Remote Similarity	NPD7331	Phase 2
0.5957	Remote Similarity	NPD5695	Phase 3
0.5955	Remote Similarity	NPD6098	Approved
0.5949	Remote Similarity	NPD4137	Phase 3
0.5949	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD15	Approved
0.5949	Remote Similarity	NPD791	Approved
0.5938	Remote Similarity	NPD5696	Approved
0.5934	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6101	Approved
0.593	Remote Similarity	NPD4139	Approved
0.593	Remote Similarity	NPD4692	Approved
0.5918	Remote Similarity	NPD5226	Approved
0.5918	Remote Similarity	NPD4633	Approved
0.5918	Remote Similarity	NPD5224	Approved
0.5918	Remote Similarity	NPD5225	Approved
0.59	Remote Similarity	NPD7128	Approved
0.59	Remote Similarity	NPD5739	Approved
0.59	Remote Similarity	NPD6402	Approved
0.59	Remote Similarity	NPD6675	Approved
0.5875	Remote Similarity	NPD4789	Approved
0.5875	Remote Similarity	NPD4691	Approved
0.5875	Remote Similarity	NPD4747	Approved
0.5875	Remote Similarity	NPD4245	Approved
0.5875	Remote Similarity	NPD4244	Approved
0.5875	Remote Similarity	NPD4787	Phase 1
0.587	Remote Similarity	NPD4096	Approved
0.587	Remote Similarity	NPD5785	Approved
0.5859	Remote Similarity	NPD5175	Approved
0.5859	Remote Similarity	NPD5174	Approved
0.5859	Remote Similarity	NPD4754	Approved
0.5859	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7900	Approved
0.5844	Remote Similarity	NPD7341	Phase 2
0.5843	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5363	Approved
0.5842	Remote Similarity	NPD6412	Phase 2
0.5823	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4159	Approved
0.5816	Remote Similarity	NPD5344	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