NPASS Compound

Structure

NPC72755 OpenBabel07101719132D 22 24 0 0 1 0 0 0 0 0999 V2000 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0491 -0.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4538 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5878 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 6 0 0 0 15 18 1 6 0 0 0 15 20 1 0 0 0 0 16 19 1 1 0 0 0 16 22 1 0 0 0 0 18 4 1 6 0 0 0 19 5 1 1 0 0 0 19 21 1 0 0 0 0 20 6 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	343.751
LogP:	4.821
LogD:	4.048
LogS:	-5.356
# Rotatable Bonds:	2
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	4.717
Fsp3:	0.9
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:	-4.664
MDCK Permeability:	1.9252505808253773e-05
Pgp-inhibitor:	0.844
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	92.77669525146484%
Volume Distribution (VD):	1.941
Pgp-substrate:	6.371548652648926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.148
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.406
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	3.988
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.105
Skin Sensitization:	0.836
Carcinogencity:	0.068
Eye Corrosion:	0.976
Eye Irritation:	0.926
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC72755

Natural Product ID:	NPC72755
*Common Name:**	(12R,13R)-8,12-Epoxy-14-Labden-13-Ol
IUPAC Name:	(2R)-2-[(2R,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran-2-yl]but-3-en-2-ol
Synonyms:
Standard InCHIKey:	OOLRCVXXZSHYDM-ZWDFGCBGSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-7-19(5,21)16-13-15-18(4)11-8-10-17(2,3)14(18)9-12-20(15,6)22-16/h7,14-16,21H,1,8-13H2,2-6H3/t14-,15+,16+,18-,19+,20+/m0/s1
SMILES:	C=C[C@](C)([C@H]1C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL538680
PubChem CID:	15241257
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19435338]
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31557016]
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1.9	ug.mL-1	PMID[538932]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	0.6	ug.mL-1	PMID[538932]

☑ 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 NPC72755 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	163
0.1-0.2	1690
0.2-0.3	6040
0.3-0.4	15372
0.4-0.5	8246
0.5-0.6	6472
0.6-0.7	3941
0.7-0.8	733
0.8-0.85	34
0.85-0.9	2
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476367
0.875	High Similarity	NPC477978
0.859	High Similarity	NPC137587
0.8554	High Similarity	NPC476948
0.8493	Intermediate Similarity	NPC117607
0.8493	Intermediate Similarity	NPC101307
0.8493	Intermediate Similarity	NPC88454
0.8193	Intermediate Similarity	NPC15534
0.8101	Intermediate Similarity	NPC470766
0.8026	Intermediate Similarity	NPC210323
0.8026	Intermediate Similarity	NPC9942
0.8	Intermediate Similarity	NPC169994
0.7952	Intermediate Similarity	NPC471408
0.7952	Intermediate Similarity	NPC155521
0.7949	Intermediate Similarity	NPC95165
0.7931	Intermediate Similarity	NPC115607
0.7931	Intermediate Similarity	NPC477917
0.7901	Intermediate Similarity	NPC148977
0.7895	Intermediate Similarity	NPC2648
0.7895	Intermediate Similarity	NPC245795
0.7889	Intermediate Similarity	NPC8774
0.7882	Intermediate Similarity	NPC164424
0.7875	Intermediate Similarity	NPC329626
0.7875	Intermediate Similarity	NPC265588
0.7875	Intermediate Similarity	NPC63958
0.7841	Intermediate Similarity	NPC291484
0.7841	Intermediate Similarity	NPC80561
0.7841	Intermediate Similarity	NPC474249
0.7841	Intermediate Similarity	NPC11216
0.7841	Intermediate Similarity	NPC204188
0.7841	Intermediate Similarity	NPC3345
0.7841	Intermediate Similarity	NPC261990
0.7841	Intermediate Similarity	NPC329596
0.7831	Intermediate Similarity	NPC476646
0.7831	Intermediate Similarity	NPC70927
0.7816	Intermediate Similarity	NPC473436
0.7816	Intermediate Similarity	NPC133588
0.7805	Intermediate Similarity	NPC233295
0.7802	Intermediate Similarity	NPC288970
0.7802	Intermediate Similarity	NPC12103
0.7802	Intermediate Similarity	NPC103165
0.7802	Intermediate Similarity	NPC227583
0.7802	Intermediate Similarity	NPC98457
0.7802	Intermediate Similarity	NPC210717
0.7791	Intermediate Similarity	NPC261266
0.7778	Intermediate Similarity	NPC65402
0.7778	Intermediate Similarity	NPC471798
0.7778	Intermediate Similarity	NPC127718
0.7763	Intermediate Similarity	NPC253303
0.7763	Intermediate Similarity	NPC269077
0.7753	Intermediate Similarity	NPC97404
0.7753	Intermediate Similarity	NPC41554
0.775	Intermediate Similarity	NPC32832
0.775	Intermediate Similarity	NPC12696
0.775	Intermediate Similarity	NPC103822
0.775	Intermediate Similarity	NPC231680
0.775	Intermediate Similarity	NPC270306
0.775	Intermediate Similarity	NPC91387
0.775	Intermediate Similarity	NPC472952
0.775	Intermediate Similarity	NPC472950
0.7727	Intermediate Similarity	NPC470361
0.7727	Intermediate Similarity	NPC97103
0.7717	Intermediate Similarity	NPC261807
0.7711	Intermediate Similarity	NPC287749
0.7711	Intermediate Similarity	NPC47149
0.7711	Intermediate Similarity	NPC96362
0.7701	Intermediate Similarity	NPC189777
0.7701	Intermediate Similarity	NPC245004
0.7692	Intermediate Similarity	NPC283316
0.7683	Intermediate Similarity	NPC83351
0.7683	Intermediate Similarity	NPC52755
0.7683	Intermediate Similarity	NPC11908
0.7683	Intermediate Similarity	NPC167891
0.7683	Intermediate Similarity	NPC472500
0.7683	Intermediate Similarity	NPC472499
0.7674	Intermediate Similarity	NPC290731
0.7674	Intermediate Similarity	NPC470360
0.7667	Intermediate Similarity	NPC27531
0.7667	Intermediate Similarity	NPC119379
0.7662	Intermediate Similarity	NPC244790
0.7662	Intermediate Similarity	NPC276616
0.7654	Intermediate Similarity	NPC91573
0.764	Intermediate Similarity	NPC295668
0.764	Intermediate Similarity	NPC191323
0.7634	Intermediate Similarity	NPC476895
0.7632	Intermediate Similarity	NPC476406
0.7625	Intermediate Similarity	NPC472503
0.7625	Intermediate Similarity	NPC306727
0.7625	Intermediate Similarity	NPC201048
0.7625	Intermediate Similarity	NPC476366
0.7625	Intermediate Similarity	NPC308440
0.7619	Intermediate Similarity	NPC249423
0.7614	Intermediate Similarity	NPC474668
0.7609	Intermediate Similarity	NPC72204
0.7595	Intermediate Similarity	NPC167706
0.759	Intermediate Similarity	NPC476316
0.759	Intermediate Similarity	NPC472463
0.759	Intermediate Similarity	NPC24504
0.7586	Intermediate Similarity	NPC94462
0.7586	Intermediate Similarity	NPC475684
0.7586	Intermediate Similarity	NPC255143
0.7586	Intermediate Similarity	NPC6391
0.7586	Intermediate Similarity	NPC299068
0.7586	Intermediate Similarity	NPC125399
0.7586	Intermediate Similarity	NPC476217
0.7582	Intermediate Similarity	NPC144202
0.7561	Intermediate Similarity	NPC91594
0.7561	Intermediate Similarity	NPC474574
0.7561	Intermediate Similarity	NPC11907
0.7561	Intermediate Similarity	NPC470758
0.7561	Intermediate Similarity	NPC470711
0.7561	Intermediate Similarity	NPC64081
0.7561	Intermediate Similarity	NPC130136
0.7561	Intermediate Similarity	NPC133596
0.7558	Intermediate Similarity	NPC474493
0.7556	Intermediate Similarity	NPC114389
0.7556	Intermediate Similarity	NPC289361
0.7556	Intermediate Similarity	NPC275671
0.7556	Intermediate Similarity	NPC210268
0.7553	Intermediate Similarity	NPC38855
0.7531	Intermediate Similarity	NPC477923
0.7531	Intermediate Similarity	NPC185536
0.7531	Intermediate Similarity	NPC36479
0.7531	Intermediate Similarity	NPC66566
0.7529	Intermediate Similarity	NPC50964
0.7529	Intermediate Similarity	NPC49964
0.7529	Intermediate Similarity	NPC218616
0.7529	Intermediate Similarity	NPC296701
0.7528	Intermediate Similarity	NPC170633
0.7528	Intermediate Similarity	NPC20946
0.7527	Intermediate Similarity	NPC26307
0.7527	Intermediate Similarity	NPC476893
0.75	Intermediate Similarity	NPC241290
0.75	Intermediate Similarity	NPC474592
0.75	Intermediate Similarity	NPC131329
0.75	Intermediate Similarity	NPC164840
0.75	Intermediate Similarity	NPC209944
0.75	Intermediate Similarity	NPC13554
0.75	Intermediate Similarity	NPC44538
0.75	Intermediate Similarity	NPC258595
0.75	Intermediate Similarity	NPC64123
0.75	Intermediate Similarity	NPC476894
0.75	Intermediate Similarity	NPC233744
0.7474	Intermediate Similarity	NPC476896
0.7473	Intermediate Similarity	NPC310013
0.7473	Intermediate Similarity	NPC98193
0.7473	Intermediate Similarity	NPC307776
0.7473	Intermediate Similarity	NPC137461
0.7471	Intermediate Similarity	NPC477578
0.7471	Intermediate Similarity	NPC274448
0.7471	Intermediate Similarity	NPC196911
0.7471	Intermediate Similarity	NPC471379
0.747	Intermediate Similarity	NPC475
0.747	Intermediate Similarity	NPC472342
0.747	Intermediate Similarity	NPC472502
0.747	Intermediate Similarity	NPC301707
0.747	Intermediate Similarity	NPC31828
0.747	Intermediate Similarity	NPC472501
0.7444	Intermediate Similarity	NPC473956
0.7444	Intermediate Similarity	NPC475751
0.7442	Intermediate Similarity	NPC5958
0.7442	Intermediate Similarity	NPC85095
0.7442	Intermediate Similarity	NPC474634
0.7442	Intermediate Similarity	NPC82623
0.7442	Intermediate Similarity	NPC216420
0.7442	Intermediate Similarity	NPC470558
0.7442	Intermediate Similarity	NPC211135
0.7442	Intermediate Similarity	NPC317458
0.7442	Intermediate Similarity	NPC132635
0.7442	Intermediate Similarity	NPC185605
0.7439	Intermediate Similarity	NPC470749
0.7439	Intermediate Similarity	NPC253190
0.7439	Intermediate Similarity	NPC293223
0.7436	Intermediate Similarity	NPC266578
0.7419	Intermediate Similarity	NPC471903
0.7419	Intermediate Similarity	NPC90583
0.7416	Intermediate Similarity	NPC280556
0.7416	Intermediate Similarity	NPC92370
0.7416	Intermediate Similarity	NPC475664
0.7416	Intermediate Similarity	NPC476723
0.7416	Intermediate Similarity	NPC470260
0.7416	Intermediate Similarity	NPC75443
0.7416	Intermediate Similarity	NPC476724
0.7412	Intermediate Similarity	NPC264245
0.7412	Intermediate Similarity	NPC471270
0.7412	Intermediate Similarity	NPC209620
0.7412	Intermediate Similarity	NPC474531
0.7412	Intermediate Similarity	NPC23852
0.7407	Intermediate Similarity	NPC71152
0.7407	Intermediate Similarity	NPC243342
0.7407	Intermediate Similarity	NPC477138
0.7407	Intermediate Similarity	NPC476736
0.7407	Intermediate Similarity	NPC470151
0.7403	Intermediate Similarity	NPC42630
0.7386	Intermediate Similarity	NPC139724
0.7386	Intermediate Similarity	NPC121981
0.7381	Intermediate Similarity	NPC477282
0.7381	Intermediate Similarity	NPC81074
0.7381	Intermediate Similarity	NPC328714
0.7375	Intermediate Similarity	NPC471268

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 NPC72755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	2113
0.2-0.3	4189
0.3-0.4	1860
0.4-0.5	457
0.5-0.6	236
0.6-0.7	122
0.7-0.8	22
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
0.75	Intermediate Similarity	NPD7524	Approved
0.7241	Intermediate Similarity	NPD6695	Phase 3
0.7159	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7525	Registered
0.7093	Intermediate Similarity	NPD6930	Phase 2
0.7093	Intermediate Similarity	NPD6931	Approved
0.7024	Intermediate Similarity	NPD6933	Approved
0.6977	Remote Similarity	NPD7645	Phase 2
0.6977	Remote Similarity	NPD6929	Approved
0.6923	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7750	Discontinued
0.6914	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4225	Approved
0.6905	Remote Similarity	NPD7339	Approved
0.6905	Remote Similarity	NPD6942	Approved
0.6897	Remote Similarity	NPD7332	Phase 2
0.6897	Remote Similarity	NPD7514	Phase 3
0.686	Remote Similarity	NPD7145	Approved
0.6824	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6926	Approved
0.6786	Remote Similarity	NPD6924	Approved
0.6744	Remote Similarity	NPD6932	Approved
0.6744	Remote Similarity	NPD6925	Approved
0.6744	Remote Similarity	NPD5776	Phase 2
0.6709	Remote Similarity	NPD371	Approved
0.6706	Remote Similarity	NPD8264	Approved
0.6703	Remote Similarity	NPD6893	Approved
0.6699	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7640	Approved
0.6632	Remote Similarity	NPD7087	Discontinued
0.6629	Remote Similarity	NPD6898	Phase 1
0.6629	Remote Similarity	NPD6902	Approved
0.6588	Remote Similarity	NPD4784	Approved
0.6588	Remote Similarity	NPD4785	Approved
0.6566	Remote Similarity	NPD7638	Approved
0.6548	Remote Similarity	NPD7152	Approved
0.6548	Remote Similarity	NPD7151	Approved
0.6548	Remote Similarity	NPD7150	Approved
0.6517	Remote Similarity	NPD7509	Discontinued
0.6436	Remote Similarity	NPD5344	Discontinued
0.6436	Remote Similarity	NPD4159	Approved
0.6429	Remote Similarity	NPD7143	Approved
0.6429	Remote Similarity	NPD7144	Approved
0.6413	Remote Similarity	NPD4786	Approved
0.6404	Remote Similarity	NPD6683	Phase 2
0.6374	Remote Similarity	NPD3667	Approved
0.6364	Remote Similarity	NPD7115	Discovery
0.6353	Remote Similarity	NPD4243	Approved
0.6344	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4748	Discontinued
0.6333	Remote Similarity	NPD6928	Phase 2
0.6329	Remote Similarity	NPD1145	Discontinued
0.631	Remote Similarity	NPD6923	Approved
0.631	Remote Similarity	NPD6922	Approved
0.6289	Remote Similarity	NPD6079	Approved
0.6289	Remote Similarity	NPD8035	Phase 2
0.6289	Remote Similarity	NPD8034	Phase 2
0.6289	Remote Similarity	NPD7637	Suspended
0.6277	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD5328	Approved
0.6235	Remote Similarity	NPD4787	Phase 1
0.6224	Remote Similarity	NPD6399	Phase 3
0.6214	Remote Similarity	NPD7632	Discontinued
0.6176	Remote Similarity	NPD6648	Approved
0.6168	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7748	Approved
0.6161	Remote Similarity	NPD7328	Approved
0.6161	Remote Similarity	NPD7327	Approved
0.614	Remote Similarity	NPD8033	Approved
0.6136	Remote Similarity	NPD3703	Phase 2
0.6111	Remote Similarity	NPD6114	Approved
0.6111	Remote Similarity	NPD6115	Approved
0.6111	Remote Similarity	NPD6697	Approved
0.6111	Remote Similarity	NPD6118	Approved
0.6106	Remote Similarity	NPD7516	Approved
0.6091	Remote Similarity	NPD4632	Approved
0.6091	Remote Similarity	NPD8133	Approved
0.6061	Remote Similarity	NPD4202	Approved
0.6061	Remote Similarity	NPD8171	Discontinued
0.6058	Remote Similarity	NPD5211	Phase 2
0.6053	Remote Similarity	NPD8377	Approved
0.6053	Remote Similarity	NPD6054	Approved
0.6053	Remote Similarity	NPD8294	Approved
0.6044	Remote Similarity	NPD4195	Approved
0.6038	Remote Similarity	NPD6640	Phase 3
0.602	Remote Similarity	NPD7136	Phase 2
0.602	Remote Similarity	NPD3168	Discontinued
0.6	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD8335	Approved
0.6	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD6921	Approved
0.6	Remote Similarity	NPD8380	Approved
0.6	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD6412	Phase 2
0.598	Remote Similarity	NPD7902	Approved
0.5977	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4634	Approved
0.5963	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.596	Remote Similarity	NPD7515	Phase 2
0.5957	Remote Similarity	NPD4788	Approved
0.5955	Remote Similarity	NPD5275	Approved
0.5955	Remote Similarity	NPD4190	Phase 3
0.5948	Remote Similarity	NPD6370	Approved
0.5943	Remote Similarity	NPD5141	Approved
0.5938	Remote Similarity	NPD4623	Approved
0.5938	Remote Similarity	NPD4519	Discontinued
0.593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6881	Approved
0.5926	Remote Similarity	NPD6899	Approved
0.5926	Remote Similarity	NPD6686	Approved
0.5918	Remote Similarity	NPD6051	Approved
0.5913	Remote Similarity	NPD6059	Approved
0.5913	Remote Similarity	NPD6319	Approved
0.59	Remote Similarity	NPD5778	Approved
0.59	Remote Similarity	NPD5779	Approved
0.5895	Remote Similarity	NPD3666	Approved
0.5895	Remote Similarity	NPD3668	Phase 3
0.5895	Remote Similarity	NPD3133	Approved
0.5895	Remote Similarity	NPD3665	Phase 1
0.5889	Remote Similarity	NPD6117	Approved
0.5888	Remote Similarity	NPD7128	Approved
0.5888	Remote Similarity	NPD6675	Approved
0.5888	Remote Similarity	NPD5739	Approved
0.5888	Remote Similarity	NPD6008	Approved
0.5888	Remote Similarity	NPD6402	Approved
0.5882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5221	Approved
0.5882	Remote Similarity	NPD5222	Approved
0.5872	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5286	Approved
0.5865	Remote Similarity	NPD4696	Approved
0.5865	Remote Similarity	NPD5285	Approved
0.5862	Remote Similarity	NPD6015	Approved
0.5862	Remote Similarity	NPD6016	Approved
0.5854	Remote Similarity	NPD368	Approved
0.5847	Remote Similarity	NPD7492	Approved
0.5843	Remote Similarity	NPD1811	Approved
0.5843	Remote Similarity	NPD1810	Approved
0.5843	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD1694	Approved
0.5825	Remote Similarity	NPD5173	Approved
0.5825	Remote Similarity	NPD4755	Approved
0.5824	Remote Similarity	NPD6116	Phase 1
0.5818	Remote Similarity	NPD7102	Approved
0.5818	Remote Similarity	NPD7290	Approved
0.5818	Remote Similarity	NPD6883	Approved
0.5814	Remote Similarity	NPD5360	Phase 3
0.5814	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5988	Approved
0.581	Remote Similarity	NPD5223	Approved
0.5798	Remote Similarity	NPD7507	Approved
0.5798	Remote Similarity	NPD6616	Approved
0.5789	Remote Similarity	NPD6009	Approved
0.578	Remote Similarity	NPD6011	Approved
0.578	Remote Similarity	NPD7320	Approved
0.5773	Remote Similarity	NPD6684	Approved
0.5773	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7334	Approved
0.5773	Remote Similarity	NPD7521	Approved
0.5773	Remote Similarity	NPD7146	Approved
0.5773	Remote Similarity	NPD5330	Approved
0.5773	Remote Similarity	NPD6409	Approved
0.5769	Remote Similarity	NPD5290	Discontinued
0.5766	Remote Similarity	NPD6847	Approved
0.5766	Remote Similarity	NPD6869	Approved
0.5766	Remote Similarity	NPD6650	Approved
0.5766	Remote Similarity	NPD6649	Approved
0.5766	Remote Similarity	NPD6617	Approved
0.5766	Remote Similarity	NPD8130	Phase 1
0.5763	Remote Similarity	NPD7604	Phase 2
0.5755	Remote Similarity	NPD5226	Approved
0.5755	Remote Similarity	NPD4633	Approved
0.5755	Remote Similarity	NPD5224	Approved
0.5755	Remote Similarity	NPD5225	Approved
0.5753	Remote Similarity	NPD386	Approved
0.5753	Remote Similarity	NPD388	Approved
0.575	Remote Similarity	NPD7078	Approved
0.573	Remote Similarity	NPD4732	Discontinued
0.5728	Remote Similarity	NPD4697	Phase 3
0.5727	Remote Similarity	NPD6014	Approved
0.5727	Remote Similarity	NPD6372	Approved
0.5727	Remote Similarity	NPD6013	Approved
0.5727	Remote Similarity	NPD6012	Approved
0.5727	Remote Similarity	NPD6373	Approved
0.5726	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD3573	Approved
0.5702	Remote Similarity	NPD7736	Approved
0.5701	Remote Similarity	NPD5175	Approved
0.5701	Remote Similarity	NPD5174	Approved
0.5688	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD5701	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