NPASS Compound

Structure

NPC476406 OpenBabel07101719522D 22 23 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 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 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 0.6340 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 3.4641 2.0000 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 0.8660 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 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 1.7321 2.0000 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 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 3 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 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 15 2 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 1 0 0 0 17 20 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 19 22 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	349.671
LogP:	3.58
LogD:	3.621
LogS:	-4.341
# 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:	4.514
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:	-4.623
MDCK Permeability:	2.4722730813664384e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.473
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.892
Plasma Protein Binding (PPB):	87.1933364868164%
Volume Distribution (VD):	0.964
Pgp-substrate:	15.601555824279785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.146
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	6.219
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.821
Skin Sensitization:	0.232
Carcinogencity:	0.028
Eye Corrosion:	0.093
Eye Irritation:	0.687
Respiratory Toxicity:	0.344

Download Data

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

Natural Product: NPC476406

Natural Product ID:	NPC476406
*Common Name:**	Torreferol
IUPAC Name:	(3S)-5-[(4aR,5R,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol
Synonyms:	Torreferol
Standard InCHIKey:	IERFAZQCIAZODG-SPACUTFJSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-6-19(4,22)13-10-16-15(2)8-9-17-18(3,14-21)11-7-12-20(16,17)5/h6,16-17,21-22H,1-2,7-14H2,3-5H3/t16?,17-,18-,19+,20+/m0/s1
SMILES:	CC1(CCCC2(C1CCC(=C)C2CCC(C)(C=C)O)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL596905
PubChem CID:	46230470
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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	24.3	ug.mL-1	PMID[555871]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[555871]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[555871]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[555871]

☑ 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 NPC476406 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	154
0.1-0.2	1584
0.2-0.3	8944
0.3-0.4	15437
0.4-0.5	7827
0.5-0.6	5869
0.6-0.7	2245
0.7-0.8	528
0.8-0.85	90
0.85-0.9	15
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC9942
0.9344	High Similarity	NPC41160
0.8923	High Similarity	NPC68703
0.8923	High Similarity	NPC69649
0.8906	High Similarity	NPC258595
0.8696	High Similarity	NPC201048
0.8696	High Similarity	NPC476366
0.8571	High Similarity	NPC32832
0.8529	High Similarity	NPC34834
0.8507	High Similarity	NPC276616
0.8507	High Similarity	NPC2648
0.8507	High Similarity	NPC245795
0.8485	Intermediate Similarity	NPC279434
0.8485	Intermediate Similarity	NPC149680
0.8462	Intermediate Similarity	NPC68656
0.8462	Intermediate Similarity	NPC101128
0.8451	Intermediate Similarity	NPC470749
0.8451	Intermediate Similarity	NPC265588
0.8429	Intermediate Similarity	NPC476736
0.8429	Intermediate Similarity	NPC306727
0.8406	Intermediate Similarity	NPC167706
0.8406	Intermediate Similarity	NPC242001
0.8382	Intermediate Similarity	NPC210323
0.8358	Intermediate Similarity	NPC101307
0.8358	Intermediate Similarity	NPC88454
0.8358	Intermediate Similarity	NPC197805
0.8358	Intermediate Similarity	NPC117607
0.8333	Intermediate Similarity	NPC470711
0.8333	Intermediate Similarity	NPC470758
0.8333	Intermediate Similarity	NPC64123
0.8333	Intermediate Similarity	NPC91594
0.8286	Intermediate Similarity	NPC471799
0.8286	Intermediate Similarity	NPC68443
0.8286	Intermediate Similarity	NPC472506
0.8286	Intermediate Similarity	NPC476609
0.8261	Intermediate Similarity	NPC283316
0.8261	Intermediate Similarity	NPC145498
0.8243	Intermediate Similarity	NPC209944
0.8243	Intermediate Similarity	NPC241290
0.8243	Intermediate Similarity	NPC164840
0.8226	Intermediate Similarity	NPC39068
0.8226	Intermediate Similarity	NPC264779
0.8219	Intermediate Similarity	NPC167891
0.8219	Intermediate Similarity	NPC83351
0.8209	Intermediate Similarity	NPC286669
0.8209	Intermediate Similarity	NPC476039
0.8209	Intermediate Similarity	NPC222366
0.8209	Intermediate Similarity	NPC475897
0.8194	Intermediate Similarity	NPC253190
0.8194	Intermediate Similarity	NPC63958
0.8182	Intermediate Similarity	NPC144650
0.8169	Intermediate Similarity	NPC471797
0.8169	Intermediate Similarity	NPC91858
0.8169	Intermediate Similarity	NPC46610
0.8169	Intermediate Similarity	NPC243342
0.8169	Intermediate Similarity	NPC477138
0.8169	Intermediate Similarity	NPC18819
0.8143	Intermediate Similarity	NPC164045
0.8143	Intermediate Similarity	NPC475077
0.8133	Intermediate Similarity	NPC264245
0.8133	Intermediate Similarity	NPC249423
0.8116	Intermediate Similarity	NPC471560
0.8108	Intermediate Similarity	NPC192999
0.8108	Intermediate Similarity	NPC476438
0.8088	Intermediate Similarity	NPC185874
0.8088	Intermediate Similarity	NPC253303
0.8088	Intermediate Similarity	NPC269077
0.8088	Intermediate Similarity	NPC139207
0.806	Intermediate Similarity	NPC2728
0.806	Intermediate Similarity	NPC282619
0.806	Intermediate Similarity	NPC27243
0.806	Intermediate Similarity	NPC208198
0.806	Intermediate Similarity	NPC11555
0.806	Intermediate Similarity	NPC172613
0.806	Intermediate Similarity	NPC60837
0.806	Intermediate Similarity	NPC476737
0.8056	Intermediate Similarity	NPC144075
0.8056	Intermediate Similarity	NPC476605
0.8056	Intermediate Similarity	NPC185536
0.8056	Intermediate Similarity	NPC291503
0.8028	Intermediate Similarity	NPC182717
0.8028	Intermediate Similarity	NPC474743
0.8028	Intermediate Similarity	NPC130665
0.8026	Intermediate Similarity	NPC49964
0.8026	Intermediate Similarity	NPC296701
0.8026	Intermediate Similarity	NPC218616
0.8	Intermediate Similarity	NPC234193
0.8	Intermediate Similarity	NPC96362
0.7973	Intermediate Similarity	NPC269543
0.7973	Intermediate Similarity	NPC474216
0.7973	Intermediate Similarity	NPC247783
0.7973	Intermediate Similarity	NPC476314
0.7973	Intermediate Similarity	NPC472342
0.7973	Intermediate Similarity	NPC11908
0.7973	Intermediate Similarity	NPC301707
0.7973	Intermediate Similarity	NPC472501
0.7971	Intermediate Similarity	NPC208999
0.7971	Intermediate Similarity	NPC471238
0.7971	Intermediate Similarity	NPC266578
0.7971	Intermediate Similarity	NPC160209
0.7971	Intermediate Similarity	NPC32055
0.7971	Intermediate Similarity	NPC244790
0.7969	Intermediate Similarity	NPC189290
0.7969	Intermediate Similarity	NPC474769
0.7945	Intermediate Similarity	NPC38141
0.7945	Intermediate Similarity	NPC247325
0.7945	Intermediate Similarity	NPC244488
0.7917	Intermediate Similarity	NPC27395
0.7917	Intermediate Similarity	NPC469533
0.7917	Intermediate Similarity	NPC469534
0.7917	Intermediate Similarity	NPC469593
0.7917	Intermediate Similarity	NPC329090
0.791	Intermediate Similarity	NPC225415
0.7895	Intermediate Similarity	NPC47761
0.7895	Intermediate Similarity	NPC476646
0.7887	Intermediate Similarity	NPC471272
0.7867	Intermediate Similarity	NPC28862
0.7867	Intermediate Similarity	NPC209430
0.7867	Intermediate Similarity	NPC47982
0.7867	Intermediate Similarity	NPC30986
0.7867	Intermediate Similarity	NPC143182
0.7867	Intermediate Similarity	NPC81306
0.7867	Intermediate Similarity	NPC109546
0.7867	Intermediate Similarity	NPC84694
0.7857	Intermediate Similarity	NPC473893
0.7857	Intermediate Similarity	NPC476604
0.7857	Intermediate Similarity	NPC234511
0.7857	Intermediate Similarity	NPC474248
0.7857	Intermediate Similarity	NPC476431
0.7838	Intermediate Similarity	NPC248830
0.7838	Intermediate Similarity	NPC119355
0.7838	Intermediate Similarity	NPC198968
0.7838	Intermediate Similarity	NPC212241
0.7838	Intermediate Similarity	NPC260301
0.7838	Intermediate Similarity	NPC318495
0.7838	Intermediate Similarity	NPC331618
0.7838	Intermediate Similarity	NPC257191
0.7838	Intermediate Similarity	NPC155986
0.7838	Intermediate Similarity	NPC138502
0.7838	Intermediate Similarity	NPC471798
0.7838	Intermediate Similarity	NPC169994
0.7838	Intermediate Similarity	NPC307336
0.7826	Intermediate Similarity	NPC171225
0.7826	Intermediate Similarity	NPC114651
0.7821	Intermediate Similarity	NPC205845
0.7808	Intermediate Similarity	NPC319090
0.7808	Intermediate Similarity	NPC103822
0.7808	Intermediate Similarity	NPC3403
0.7808	Intermediate Similarity	NPC66566
0.7808	Intermediate Similarity	NPC477923
0.7808	Intermediate Similarity	NPC328104
0.7794	Intermediate Similarity	NPC163678
0.7792	Intermediate Similarity	NPC155521
0.7792	Intermediate Similarity	NPC50964
0.7792	Intermediate Similarity	NPC87489
0.7792	Intermediate Similarity	NPC2524
0.7778	Intermediate Similarity	NPC474140
0.7778	Intermediate Similarity	NPC211009
0.7763	Intermediate Similarity	NPC324772
0.7763	Intermediate Similarity	NPC281880
0.7763	Intermediate Similarity	NPC295131
0.7761	Intermediate Similarity	NPC81615
0.7761	Intermediate Similarity	NPC174956
0.7746	Intermediate Similarity	NPC189745
0.7746	Intermediate Similarity	NPC45296
0.7746	Intermediate Similarity	NPC475728
0.7746	Intermediate Similarity	NPC91369
0.7733	Intermediate Similarity	NPC239098
0.7733	Intermediate Similarity	NPC473943
0.7733	Intermediate Similarity	NPC477514
0.7733	Intermediate Similarity	NPC285761
0.7733	Intermediate Similarity	NPC472499
0.7733	Intermediate Similarity	NPC475
0.7733	Intermediate Similarity	NPC472502
0.7733	Intermediate Similarity	NPC137587
0.7733	Intermediate Similarity	NPC472500
0.7722	Intermediate Similarity	NPC164424
0.7722	Intermediate Similarity	NPC274448
0.7714	Intermediate Similarity	NPC216460
0.7714	Intermediate Similarity	NPC96484
0.7714	Intermediate Similarity	NPC94192
0.7703	Intermediate Similarity	NPC321381
0.7703	Intermediate Similarity	NPC106432
0.7703	Intermediate Similarity	NPC476607
0.7703	Intermediate Similarity	NPC91573
0.7703	Intermediate Similarity	NPC477925
0.7703	Intermediate Similarity	NPC129165
0.7703	Intermediate Similarity	NPC476606
0.7703	Intermediate Similarity	NPC315261
0.7703	Intermediate Similarity	NPC274079
0.7703	Intermediate Similarity	NPC113733
0.7703	Intermediate Similarity	NPC107059
0.7703	Intermediate Similarity	NPC134330
0.7703	Intermediate Similarity	NPC321016
0.7692	Intermediate Similarity	NPC474634
0.7692	Intermediate Similarity	NPC82623
0.7692	Intermediate Similarity	NPC475789
0.7681	Intermediate Similarity	NPC250977
0.7681	Intermediate Similarity	NPC473929
0.7681	Intermediate Similarity	NPC202017

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 NPC476406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	2084
0.2-0.3	4206
0.3-0.4	1927
0.4-0.5	453
0.5-0.6	239
0.6-0.7	71
0.7-0.8	34
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
0.7917	Intermediate Similarity	NPD6924	Approved
0.7917	Intermediate Similarity	NPD6926	Approved
0.7763	Intermediate Similarity	NPD6930	Phase 2
0.7763	Intermediate Similarity	NPD6931	Approved
0.7733	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6933	Approved
0.7632	Intermediate Similarity	NPD6929	Approved
0.7568	Intermediate Similarity	NPD8264	Approved
0.7568	Intermediate Similarity	NPD7339	Approved
0.7568	Intermediate Similarity	NPD6942	Approved
0.7532	Intermediate Similarity	NPD7525	Registered
0.7532	Intermediate Similarity	NPD7332	Phase 2
0.7532	Intermediate Similarity	NPD7514	Phase 3
0.75	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD7145	Approved
0.75	Intermediate Similarity	NPD7143	Approved
0.7468	Intermediate Similarity	NPD6695	Phase 3
0.7467	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4785	Approved
0.7432	Intermediate Similarity	NPD4784	Approved
0.7403	Intermediate Similarity	NPD7645	Phase 2
0.7397	Intermediate Similarity	NPD7150	Approved
0.7397	Intermediate Similarity	NPD7151	Approved
0.7397	Intermediate Similarity	NPD4243	Approved
0.7397	Intermediate Similarity	NPD7152	Approved
0.7375	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5776	Phase 2
0.7368	Intermediate Similarity	NPD6925	Approved
0.7368	Intermediate Similarity	NPD6932	Approved
0.7361	Intermediate Similarity	NPD6923	Approved
0.7361	Intermediate Similarity	NPD6922	Approved
0.7308	Intermediate Similarity	NPD7509	Discontinued
0.7284	Intermediate Similarity	NPD6893	Approved
0.7215	Intermediate Similarity	NPD6902	Approved
0.7215	Intermediate Similarity	NPD6898	Phase 1
0.7108	Intermediate Similarity	NPD7524	Approved
0.7108	Intermediate Similarity	NPD7750	Discontinued
0.7108	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4788	Approved
0.6962	Remote Similarity	NPD6683	Phase 2
0.6962	Remote Similarity	NPD4195	Approved
0.6951	Remote Similarity	NPD4786	Approved
0.6914	Remote Similarity	NPD3667	Approved
0.6883	Remote Similarity	NPD4190	Phase 3
0.6883	Remote Similarity	NPD5275	Approved
0.6857	Remote Similarity	NPD368	Approved
0.6786	Remote Similarity	NPD4623	Approved
0.6786	Remote Similarity	NPD4519	Discontinued
0.6782	Remote Similarity	NPD7087	Discontinued
0.6747	Remote Similarity	NPD3133	Approved
0.6747	Remote Similarity	NPD3666	Approved
0.6747	Remote Similarity	NPD3665	Phase 1
0.6716	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4219	Approved
0.6591	Remote Similarity	NPD6079	Approved
0.6588	Remote Similarity	NPD3618	Phase 1
0.6552	Remote Similarity	NPD4753	Phase 2
0.6552	Remote Similarity	NPD5328	Approved
0.6506	Remote Similarity	NPD4223	Phase 3
0.6506	Remote Similarity	NPD4221	Approved
0.6477	Remote Similarity	NPD7136	Phase 2
0.6471	Remote Similarity	NPD5329	Approved
0.6463	Remote Similarity	NPD4695	Discontinued
0.6463	Remote Similarity	NPD4748	Discontinued
0.6447	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4732	Discontinued
0.6404	Remote Similarity	NPD7637	Suspended
0.6404	Remote Similarity	NPD7515	Phase 2
0.6395	Remote Similarity	NPD5279	Phase 3
0.6374	Remote Similarity	NPD5210	Approved
0.6374	Remote Similarity	NPD4629	Approved
0.6364	Remote Similarity	NPD4787	Phase 1
0.6353	Remote Similarity	NPD4197	Approved
0.6351	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4202	Approved
0.6316	Remote Similarity	NPD5211	Phase 2
0.6277	Remote Similarity	NPD7640	Approved
0.6277	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD6084	Phase 2
0.6237	Remote Similarity	NPD6083	Phase 2
0.622	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5690	Phase 2
0.6207	Remote Similarity	NPD5205	Approved
0.6207	Remote Similarity	NPD4688	Approved
0.6207	Remote Similarity	NPD4138	Approved
0.6207	Remote Similarity	NPD4689	Approved
0.6207	Remote Similarity	NPD4690	Approved
0.6207	Remote Similarity	NPD4693	Phase 3
0.6186	Remote Similarity	NPD5141	Approved
0.618	Remote Similarity	NPD6051	Approved
0.617	Remote Similarity	NPD4225	Approved
0.617	Remote Similarity	NPD7638	Approved
0.6163	Remote Similarity	NPD3668	Phase 3
0.6154	Remote Similarity	NPD4244	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD4789	Approved
0.6154	Remote Similarity	NPD4245	Approved
0.6129	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5221	Approved
0.6129	Remote Similarity	NPD5222	Approved
0.6129	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5286	Approved
0.6105	Remote Similarity	NPD4696	Approved
0.6105	Remote Similarity	NPD5285	Approved
0.6104	Remote Similarity	NPD6705	Phase 1
0.6087	Remote Similarity	NPD7748	Approved
0.6076	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4821	Approved
0.6071	Remote Similarity	NPD4822	Approved
0.6071	Remote Similarity	NPD4820	Approved
0.6071	Remote Similarity	NPD4819	Approved
0.6067	Remote Similarity	NPD4723	Approved
0.6067	Remote Similarity	NPD4722	Approved
0.6064	Remote Similarity	NPD4755	Approved
0.6064	Remote Similarity	NPD5173	Approved
0.6044	Remote Similarity	NPD8035	Phase 2
0.6044	Remote Similarity	NPD6411	Approved
0.6044	Remote Similarity	NPD8034	Phase 2
0.6042	Remote Similarity	NPD5223	Approved
0.6027	Remote Similarity	NPD1145	Discontinued
0.6026	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD3698	Phase 2
0.6026	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD3617	Approved
0.6023	Remote Similarity	NPD4694	Approved
0.6023	Remote Similarity	NPD7521	Approved
0.6023	Remote Similarity	NPD5330	Approved
0.6023	Remote Similarity	NPD7334	Approved
0.6023	Remote Similarity	NPD6409	Approved
0.6023	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7146	Approved
0.6023	Remote Similarity	NPD5280	Approved
0.6023	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD5290	Discontinued
0.6	Remote Similarity	NPD385	Approved
0.6	Remote Similarity	NPD384	Approved
0.5979	Remote Similarity	NPD5225	Approved
0.5979	Remote Similarity	NPD4633	Approved
0.5979	Remote Similarity	NPD5224	Approved
0.5979	Remote Similarity	NPD5226	Approved
0.5978	Remote Similarity	NPD5779	Approved
0.5978	Remote Similarity	NPD5778	Approved
0.5957	Remote Similarity	NPD4697	Phase 3
0.5938	Remote Similarity	NPD4700	Approved
0.5926	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5174	Approved
0.5918	Remote Similarity	NPD5175	Approved
0.5909	Remote Similarity	NPD1696	Phase 3
0.5897	Remote Similarity	NPD5360	Phase 3
0.5897	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7902	Approved
0.5889	Remote Similarity	NPD5737	Approved
0.5889	Remote Similarity	NPD6672	Approved
0.5889	Remote Similarity	NPD6903	Approved
0.5889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5281	Approved
0.587	Remote Similarity	NPD5284	Approved
0.5862	Remote Similarity	NPD5331	Approved
0.5862	Remote Similarity	NPD5362	Discontinued
0.5862	Remote Similarity	NPD5332	Approved
0.5851	Remote Similarity	NPD5695	Phase 3
0.5846	Remote Similarity	NPD388	Approved
0.5846	Remote Similarity	NPD4265	Approved
0.5846	Remote Similarity	NPD386	Approved
0.5844	Remote Similarity	NPD7331	Phase 2
0.5843	Remote Similarity	NPD6098	Approved
0.5842	Remote Similarity	NPD6899	Approved
0.5842	Remote Similarity	NPD6881	Approved
0.5833	Remote Similarity	NPD5696	Approved
0.5833	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD4271	Approved
0.5824	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6101	Approved
0.5824	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4139	Approved
0.5814	Remote Similarity	NPD4692	Approved
0.5814	Remote Similarity	NPD4790	Discontinued
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6675	Approved
0.5795	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6117	Approved
0.5778	Remote Similarity	NPD3573	Approved
0.5761	Remote Similarity	NPD4096	Approved
0.5758	Remote Similarity	NPD4754	Approved
0.5747	Remote Similarity	NPD4270	Approved
0.5747	Remote Similarity	NPD4269	Approved
0.5745	Remote Similarity	NPD5771	Approved
0.5743	Remote Similarity	NPD5697	Approved
0.5733	Remote Similarity	NPD4192	Approved
0.5733	Remote Similarity	NPD4191	Approved
0.5733	Remote Similarity	NPD4194	Approved
0.5733	Remote Similarity	NPD4193	Approved
0.5728	Remote Similarity	NPD7102	Approved
0.5728	Remote Similarity	NPD7290	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