NPASS Compound

Structure

NPC250977 OpenBabel07101719152D 22 22 0 0 1 0 0 0 0 0999 V2000 -1.2247 1.2247 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 14 2 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 16 15 1 6 0 0 0 17 20 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 1 0 0 0 19 22 1 0 0 0 0 20 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	355.591
LogP:	3.986
LogD:	3.797
LogS:	-4.051
# Rotatable Bonds:	6
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	4.588
Fsp3:	0.7
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:	-4.572
MDCK Permeability:	2.0282290279283188e-05
Pgp-inhibitor:	0.761
Pgp-substrate:	0.148
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.832
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	89.58495330810547%
Volume Distribution (VD):	1.35
Pgp-substrate:	8.479804992675781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.748
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.836
CYP3A4-inhibitor:	0.554
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	3.745
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.516
Carcinogencity:	0.053
Eye Corrosion:	0.652
Eye Irritation:	0.912
Respiratory Toxicity:	0.608

Download Data

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

Natural Product: NPC250977

Natural Product ID:	NPC250977
*Common Name:**	(R)-2-Methyl-6-((1S,3R,4R)-4-Methyl-3-(Prop-1-En-2-Yl)-4-Vinylcyclohexyl)Hept-5-Ene-2,3-Diol
IUPAC Name:	(E,3R)-6-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-2-methylhept-5-ene-2,3-diol
Synonyms:
Standard InCHIKey:	CFHHZCDUEIUCET-JZXJGBJOSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-8-20(7)12-11-16(13-17(20)14(2)3)15(4)9-10-18(21)19(5,6)22/h8-9,16-18,21-22H,1-2,10-13H2,3-7H3/b15-9+/t16-,17+,18+,20-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)/C(=C/C[C@H](C(O)(C)C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505075
PubChem CID:	15726505
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
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209732]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	Mindoro, Philippines	n.a.	PMID[9548875]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	17.0	mm	PMID[481327]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	14.0	mm	PMID[481327]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	9.0	mm	PMID[481327]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	6.0	mm	PMID[481327]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	10.5	ug.mL-1	PMID[481327]

☑ 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 NPC250977 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	144
0.1-0.2	1566
0.2-0.3	10450
0.3-0.4	14434
0.4-0.5	8067
0.5-0.6	6154
0.6-0.7	1621
0.7-0.8	249
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8696	High Similarity	NPC104644
0.8529	High Similarity	NPC189745
0.8308	Intermediate Similarity	NPC283247
0.8286	Intermediate Similarity	NPC471799
0.8243	Intermediate Similarity	NPC474592
0.8235	Intermediate Similarity	NPC208999
0.8219	Intermediate Similarity	NPC167891
0.8219	Intermediate Similarity	NPC83351
0.8194	Intermediate Similarity	NPC265588
0.8182	Intermediate Similarity	NPC290367
0.8169	Intermediate Similarity	NPC471797
0.8143	Intermediate Similarity	NPC242001
0.8143	Intermediate Similarity	NPC167706
0.8108	Intermediate Similarity	NPC233295
0.8108	Intermediate Similarity	NPC328714
0.8088	Intermediate Similarity	NPC114651
0.8082	Intermediate Similarity	NPC325946
0.8056	Intermediate Similarity	NPC477923
0.8056	Intermediate Similarity	NPC66566
0.8	Intermediate Similarity	NPC34834
0.8	Intermediate Similarity	NPC145498
0.7945	Intermediate Similarity	NPC477925
0.7945	Intermediate Similarity	NPC274079
0.7945	Intermediate Similarity	NPC315261
0.7941	Intermediate Similarity	NPC476039
0.7941	Intermediate Similarity	NPC286669
0.7941	Intermediate Similarity	NPC222366
0.7922	Intermediate Similarity	NPC23748
0.7917	Intermediate Similarity	NPC243342
0.7917	Intermediate Similarity	NPC477138
0.791	Intermediate Similarity	NPC225415
0.7887	Intermediate Similarity	NPC242992
0.7879	Intermediate Similarity	NPC475251
0.7857	Intermediate Similarity	NPC473893
0.7838	Intermediate Similarity	NPC318495
0.7838	Intermediate Similarity	NPC198968
0.7838	Intermediate Similarity	NPC91594
0.7838	Intermediate Similarity	NPC155986
0.7838	Intermediate Similarity	NPC471798
0.7838	Intermediate Similarity	NPC477924
0.7838	Intermediate Similarity	NPC130136
0.7826	Intermediate Similarity	NPC197805
0.7812	Intermediate Similarity	NPC11130
0.7808	Intermediate Similarity	NPC291503
0.7794	Intermediate Similarity	NPC163678
0.7778	Intermediate Similarity	NPC474140
0.7778	Intermediate Similarity	NPC68443
0.7778	Intermediate Similarity	NPC182717
0.7763	Intermediate Similarity	NPC13554
0.7763	Intermediate Similarity	NPC164840
0.7763	Intermediate Similarity	NPC209944
0.7763	Intermediate Similarity	NPC241290
0.7763	Intermediate Similarity	NPC287749
0.7746	Intermediate Similarity	NPC49422
0.7746	Intermediate Similarity	NPC92801
0.7746	Intermediate Similarity	NPC9161
0.7727	Intermediate Similarity	NPC176621
0.7703	Intermediate Similarity	NPC113733
0.7703	Intermediate Similarity	NPC321381
0.7703	Intermediate Similarity	NPC107059
0.7703	Intermediate Similarity	NPC321016
0.7692	Intermediate Similarity	NPC474634
0.7692	Intermediate Similarity	NPC181872
0.7692	Intermediate Similarity	NPC49208
0.7681	Intermediate Similarity	NPC149680
0.7681	Intermediate Similarity	NPC279434
0.7681	Intermediate Similarity	NPC476406
0.7681	Intermediate Similarity	NPC267027
0.7671	Intermediate Similarity	NPC201048
0.7671	Intermediate Similarity	NPC91858
0.7671	Intermediate Similarity	NPC329090
0.7671	Intermediate Similarity	NPC27395
0.7671	Intermediate Similarity	NPC476366
0.7662	Intermediate Similarity	NPC474531
0.7662	Intermediate Similarity	NPC264245
0.7662	Intermediate Similarity	NPC47761
0.7639	Intermediate Similarity	NPC110799
0.7639	Intermediate Similarity	NPC164022
0.7639	Intermediate Similarity	NPC471268
0.7639	Intermediate Similarity	NPC471271
0.7632	Intermediate Similarity	NPC291379
0.7606	Intermediate Similarity	NPC9942
0.7606	Intermediate Similarity	NPC167272
0.7606	Intermediate Similarity	NPC471560
0.7606	Intermediate Similarity	NPC269877
0.76	Intermediate Similarity	NPC470711
0.76	Intermediate Similarity	NPC470758
0.7571	Intermediate Similarity	NPC68703
0.7571	Intermediate Similarity	NPC69649
0.7571	Intermediate Similarity	NPC45782
0.7568	Intermediate Similarity	NPC328104
0.7568	Intermediate Similarity	NPC69383
0.7568	Intermediate Similarity	NPC134847
0.7568	Intermediate Similarity	NPC12696
0.7568	Intermediate Similarity	NPC288035
0.7568	Intermediate Similarity	NPC285893
0.7568	Intermediate Similarity	NPC304309
0.7568	Intermediate Similarity	NPC136188
0.7568	Intermediate Similarity	NPC22105
0.7568	Intermediate Similarity	NPC32832
0.7568	Intermediate Similarity	NPC313179
0.7568	Intermediate Similarity	NPC319090
0.7568	Intermediate Similarity	NPC28657
0.7568	Intermediate Similarity	NPC162742
0.7568	Intermediate Similarity	NPC171148
0.7568	Intermediate Similarity	NPC230301
0.7564	Intermediate Similarity	NPC30166
0.7564	Intermediate Similarity	NPC471408
0.7564	Intermediate Similarity	NPC49964
0.7536	Intermediate Similarity	NPC471200
0.7534	Intermediate Similarity	NPC130665
0.7532	Intermediate Similarity	NPC236112
0.7532	Intermediate Similarity	NPC234193
0.75	Intermediate Similarity	NPC22955
0.75	Intermediate Similarity	NPC99168
0.75	Intermediate Similarity	NPC87604
0.75	Intermediate Similarity	NPC285761
0.75	Intermediate Similarity	NPC76931
0.75	Intermediate Similarity	NPC477522
0.75	Intermediate Similarity	NPC474216
0.75	Intermediate Similarity	NPC474989
0.75	Intermediate Similarity	NPC473943
0.75	Intermediate Similarity	NPC281590
0.75	Intermediate Similarity	NPC18603
0.75	Intermediate Similarity	NPC470396
0.75	Intermediate Similarity	NPC307965
0.75	Intermediate Similarity	NPC275910
0.7468	Intermediate Similarity	NPC317458
0.7468	Intermediate Similarity	NPC207013
0.7467	Intermediate Similarity	NPC106364
0.7467	Intermediate Similarity	NPC1973
0.7467	Intermediate Similarity	NPC167873
0.7467	Intermediate Similarity	NPC134330
0.7467	Intermediate Similarity	NPC129165
0.7467	Intermediate Similarity	NPC300324
0.7467	Intermediate Similarity	NPC240604
0.7467	Intermediate Similarity	NPC96319
0.7467	Intermediate Similarity	NPC106432
0.7467	Intermediate Similarity	NPC470749
0.7467	Intermediate Similarity	NPC470362
0.7465	Intermediate Similarity	NPC160209
0.7465	Intermediate Similarity	NPC32055
0.7465	Intermediate Similarity	NPC244790
0.7465	Intermediate Similarity	NPC216460
0.7465	Intermediate Similarity	NPC471238
0.7463	Intermediate Similarity	NPC471081
0.7436	Intermediate Similarity	NPC6707
0.7436	Intermediate Similarity	NPC476646
0.7432	Intermediate Similarity	NPC306727
0.7432	Intermediate Similarity	NPC78527
0.7432	Intermediate Similarity	NPC100334
0.7429	Intermediate Similarity	NPC326310
0.7429	Intermediate Similarity	NPC202017
0.7407	Intermediate Similarity	NPC94462
0.7403	Intermediate Similarity	NPC84694
0.7403	Intermediate Similarity	NPC80530
0.7403	Intermediate Similarity	NPC81306
0.7403	Intermediate Similarity	NPC100906
0.7403	Intermediate Similarity	NPC28862
0.7403	Intermediate Similarity	NPC53744
0.7403	Intermediate Similarity	NPC47982
0.7403	Intermediate Similarity	NPC109546
0.7403	Intermediate Similarity	NPC472463
0.7403	Intermediate Similarity	NPC143182
0.7403	Intermediate Similarity	NPC273410
0.7397	Intermediate Similarity	NPC477792
0.7397	Intermediate Similarity	NPC471272
0.7391	Intermediate Similarity	NPC101128
0.7385	Intermediate Similarity	NPC39068
0.7375	Intermediate Similarity	NPC238992
0.7375	Intermediate Similarity	NPC205845
0.7375	Intermediate Similarity	NPC474493
0.7375	Intermediate Similarity	NPC238485
0.7375	Intermediate Similarity	NPC83702
0.7375	Intermediate Similarity	NPC185568
0.7368	Intermediate Similarity	NPC90979
0.7368	Intermediate Similarity	NPC283619
0.7368	Intermediate Similarity	NPC214570
0.7368	Intermediate Similarity	NPC34019
0.7368	Intermediate Similarity	NPC34177
0.7368	Intermediate Similarity	NPC40394
0.7368	Intermediate Similarity	NPC157996
0.7368	Intermediate Similarity	NPC472805
0.7368	Intermediate Similarity	NPC101475
0.7361	Intermediate Similarity	NPC474248
0.7361	Intermediate Similarity	NPC476431
0.7361	Intermediate Similarity	NPC210323
0.7353	Intermediate Similarity	NPC469728
0.7342	Intermediate Similarity	NPC212083
0.7342	Intermediate Similarity	NPC218616
0.7342	Intermediate Similarity	NPC50964
0.7342	Intermediate Similarity	NPC87489
0.7342	Intermediate Similarity	NPC296701
0.7342	Intermediate Similarity	NPC47763
0.7333	Intermediate Similarity	NPC141071
0.7333	Intermediate Similarity	NPC257347
0.7333	Intermediate Similarity	NPC471723
0.7333	Intermediate Similarity	NPC476605
0.7333	Intermediate Similarity	NPC471468
0.7317	Intermediate Similarity	NPC174273

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 NPC250977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	2066
0.2-0.3	4285
0.3-0.4	1934
0.4-0.5	435
0.5-0.6	233
0.6-0.7	41
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7945	Intermediate Similarity	NPD6933	Approved
0.7746	Intermediate Similarity	NPD7144	Approved
0.7746	Intermediate Similarity	NPD7143	Approved
0.7671	Intermediate Similarity	NPD6926	Approved
0.7671	Intermediate Similarity	NPD6924	Approved
0.7639	Intermediate Similarity	NPD7152	Approved
0.7639	Intermediate Similarity	NPD7151	Approved
0.7639	Intermediate Similarity	NPD7150	Approved
0.7606	Intermediate Similarity	NPD6922	Approved
0.7606	Intermediate Similarity	NPD6923	Approved
0.76	Intermediate Similarity	NPD6932	Approved
0.7568	Intermediate Similarity	NPD8264	Approved
0.7568	Intermediate Similarity	NPD7339	Approved
0.7568	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7332	Phase 2
0.7308	Intermediate Similarity	NPD7525	Registered
0.7308	Intermediate Similarity	NPD7514	Phase 3
0.7273	Intermediate Similarity	NPD7145	Approved
0.72	Intermediate Similarity	NPD4784	Approved
0.72	Intermediate Similarity	NPD4785	Approved
0.7179	Intermediate Similarity	NPD6683	Phase 2
0.7179	Intermediate Similarity	NPD7645	Phase 2
0.7143	Intermediate Similarity	NPD6925	Approved
0.7143	Intermediate Similarity	NPD5776	Phase 2
0.7101	Intermediate Similarity	NPD368	Approved
0.7089	Intermediate Similarity	NPD7509	Discontinued
0.7089	Intermediate Similarity	NPD6930	Phase 2
0.7089	Intermediate Similarity	NPD6931	Approved
0.7	Intermediate Similarity	NPD6898	Phase 1
0.7	Intermediate Similarity	NPD6902	Approved
0.6962	Remote Similarity	NPD6929	Approved
0.6951	Remote Similarity	NPD4786	Approved
0.6933	Remote Similarity	NPD4243	Approved
0.6914	Remote Similarity	NPD3667	Approved
0.6905	Remote Similarity	NPD7524	Approved
0.6866	Remote Similarity	NPD4219	Approved
0.6829	Remote Similarity	NPD6695	Phase 3
0.6747	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6623	Remote Similarity	NPD4732	Discontinued
0.6548	Remote Similarity	NPD3666	Approved
0.6548	Remote Similarity	NPD3133	Approved
0.6548	Remote Similarity	NPD3665	Phase 1
0.6543	Remote Similarity	NPD4195	Approved
0.6512	Remote Similarity	NPD7750	Discontinued
0.6463	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4190	Phase 3
0.6456	Remote Similarity	NPD5275	Approved
0.6404	Remote Similarity	NPD6079	Approved
0.6395	Remote Similarity	NPD3618	Phase 1
0.6393	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5328	Approved
0.6292	Remote Similarity	NPD7136	Phase 2
0.6232	Remote Similarity	NPD342	Phase 1
0.6222	Remote Similarity	NPD7087	Discontinued
0.6222	Remote Similarity	NPD7515	Phase 2
0.6222	Remote Similarity	NPD7637	Suspended
0.622	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5279	Phase 3
0.618	Remote Similarity	NPD4753	Phase 2
0.6163	Remote Similarity	NPD3668	Phase 3
0.6154	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6118	Remote Similarity	NPD4221	Approved
0.6118	Remote Similarity	NPD4223	Phase 3
0.6092	Remote Similarity	NPD5329	Approved
0.6071	Remote Similarity	NPD4821	Approved
0.6071	Remote Similarity	NPD4695	Discontinued
0.6071	Remote Similarity	NPD4822	Approved
0.6071	Remote Similarity	NPD4819	Approved
0.6071	Remote Similarity	NPD4820	Approved
0.6047	Remote Similarity	NPD4788	Approved
0.6044	Remote Similarity	NPD6411	Approved
0.6026	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD4137	Phase 3
0.6023	Remote Similarity	NPD4519	Discontinued
0.6023	Remote Similarity	NPD5690	Phase 2
0.6023	Remote Similarity	NPD4623	Approved
0.6022	Remote Similarity	NPD4629	Approved
0.6022	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5977	Remote Similarity	NPD4197	Approved
0.5977	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5222	Approved
0.5957	Remote Similarity	NPD5221	Approved
0.5949	Remote Similarity	NPD4691	Approved
0.5949	Remote Similarity	NPD4747	Approved
0.5946	Remote Similarity	NPD4192	Approved
0.5946	Remote Similarity	NPD4191	Approved
0.5946	Remote Similarity	NPD4193	Approved
0.5946	Remote Similarity	NPD4194	Approved
0.5938	Remote Similarity	NPD5285	Approved
0.5938	Remote Similarity	NPD4696	Approved
0.5938	Remote Similarity	NPD5286	Approved
0.5926	Remote Similarity	NPD5733	Approved
0.5926	Remote Similarity	NPD4687	Approved
0.5926	Remote Similarity	NPD4058	Approved
0.5914	Remote Similarity	NPD7748	Approved
0.5909	Remote Similarity	NPD1696	Phase 3
0.5909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6084	Phase 2
0.5895	Remote Similarity	NPD6083	Phase 2
0.5895	Remote Similarity	NPD4755	Approved
0.5895	Remote Similarity	NPD5173	Approved
0.5876	Remote Similarity	NPD5344	Discontinued
0.5876	Remote Similarity	NPD5223	Approved
0.5862	Remote Similarity	NPD5331	Approved
0.5862	Remote Similarity	NPD5362	Discontinued
0.5862	Remote Similarity	NPD5332	Approved
0.5846	Remote Similarity	NPD4265	Approved
0.5844	Remote Similarity	NPD7331	Phase 2
0.5843	Remote Similarity	NPD7334	Approved
0.5843	Remote Similarity	NPD5280	Approved
0.5843	Remote Similarity	NPD4690	Approved
0.5843	Remote Similarity	NPD7146	Approved
0.5843	Remote Similarity	NPD4693	Phase 3
0.5843	Remote Similarity	NPD4694	Approved
0.5843	Remote Similarity	NPD6684	Approved
0.5843	Remote Similarity	NPD5330	Approved
0.5843	Remote Similarity	NPD7521	Approved
0.5843	Remote Similarity	NPD6409	Approved
0.5843	Remote Similarity	NPD4688	Approved
0.5843	Remote Similarity	NPD4689	Approved
0.5843	Remote Similarity	NPD4138	Approved
0.5843	Remote Similarity	NPD5205	Approved
0.5833	Remote Similarity	NPD7638	Approved
0.5833	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD5290	Discontinued
0.5833	Remote Similarity	NPD4271	Approved
0.5824	Remote Similarity	NPD6101	Approved
0.5824	Remote Similarity	NPD6051	Approved
0.5824	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD8262	Approved
0.5816	Remote Similarity	NPD5224	Approved
0.5816	Remote Similarity	NPD5225	Approved
0.5816	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD5226	Approved
0.5816	Remote Similarity	NPD4633	Approved
0.5814	Remote Similarity	NPD4790	Discontinued
0.5789	Remote Similarity	NPD3197	Phase 1
0.5789	Remote Similarity	NPD4697	Phase 3
0.5773	Remote Similarity	NPD7639	Approved
0.5773	Remote Similarity	NPD7640	Approved
0.5773	Remote Similarity	NPD4700	Approved
0.5758	Remote Similarity	NPD5175	Approved
0.5758	Remote Similarity	NPD5174	Approved
0.5753	Remote Similarity	NPD287	Approved
0.5747	Remote Similarity	NPD4270	Approved
0.5747	Remote Similarity	NPD4269	Approved
0.5743	Remote Similarity	NPD6412	Phase 2
0.5729	Remote Similarity	NPD7902	Approved
0.5728	Remote Similarity	NPD4634	Approved
0.5714	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6903	Approved
0.5714	Remote Similarity	NPD4723	Approved
0.5714	Remote Similarity	NPD4722	Approved
0.5714	Remote Similarity	NPD4159	Approved
0.5701	Remote Similarity	NPD7115	Discovery
0.57	Remote Similarity	NPD5141	Approved
0.5699	Remote Similarity	NPD5284	Approved
0.5699	Remote Similarity	NPD5281	Approved
0.5698	Remote Similarity	NPD5368	Approved
0.5698	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD4252	Approved
0.5686	Remote Similarity	NPD6881	Approved
0.5686	Remote Similarity	NPD6899	Approved
0.5684	Remote Similarity	NPD5695	Phase 3
0.5682	Remote Similarity	NPD7154	Phase 3
0.5679	Remote Similarity	NPD5276	Approved
0.5667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD3617	Approved
0.5644	Remote Similarity	NPD7128	Approved
0.5644	Remote Similarity	NPD6675	Approved
0.5644	Remote Similarity	NPD5739	Approved
0.5644	Remote Similarity	NPD6640	Phase 3
0.5644	Remote Similarity	NPD6402	Approved
0.5638	Remote Similarity	NPD5779	Approved
0.5638	Remote Similarity	NPD5778	Approved
0.5632	Remote Similarity	NPD4692	Approved
0.5632	Remote Similarity	NPD4139	Approved
0.5625	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD8297	Approved
0.5618	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4754	Approved
0.56	Remote Similarity	NPD1145	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