NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	421.16
Volume:	428.635
LogP:	3.083
LogD:	2.929
LogS:	-3.847
# Rotatable Bonds:	9
TPSA:	110.71
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	3.782
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.858
MDCK Permeability:	1.4285464203567244e-05
Pgp-inhibitor:	0.85
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.835
Plasma Protein Binding (PPB):	89.3285903930664%
Volume Distribution (VD):	0.749
Pgp-substrate:	10.201001167297363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.941
CYP2C9-substrate:	0.471
CYP2D6-inhibitor:	0.727
CYP2D6-substrate:	0.248
CYP3A4-inhibitor:	0.916
CYP3A4-substrate:	0.624

ADMET: Excretion

Clearance (CL):	4.103
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.944
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.528
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.678
Carcinogencity:	0.914
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC477978

Natural Product ID:	NPC477978
*Common Name:**	(1aR,2R,3aR,4S,5R,7aR,7bS)-4-(3-hydroxy-3-methylpent-4-enyl)-4,5,7a,7b-tetramethyl-2,3,3a,5,6,7-hexahydro-1aH-naphtho[1,2-b]oxiren-2-ol
IUPAC Name:	(1aR,2R,3aR,4S,5R,7aR,7bS)-4-(3-hydroxy-3-methylpent-4-enyl)-4,5,7a,7b-tetramethyl-2,3,3a,5,6,7-hexahydro-1aH-naphtho[1,2-b]oxiren-2-ol
Synonyms:
Standard InCHIKey:	ODARRAGDSAHHEW-WETOVQBQSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-7-17(3,22)10-11-18(4)13(2)8-9-19(5)15(18)12-14(21)16-20(19,6)23-16/h7,13-16,21-22H,1,8-12H2,2-6H3/t13-,14-,15-,16-,17?,18+,19-,20-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC(C)(C=C)O)C[C@H]([C@@H]3[C@]2(O3)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118726287
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO33595	Stachys glutinosa	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25562563]

☑ 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
Ki	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	Ki	=	25000	nM	PMID[25562563]
NPT1168	Individual Protein	Mu opioid receptor	Mus musculus	Ki	>	50000	nM	PMID[25562563]

☑ 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 NPC477978 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	237
0.1-0.2	2255
0.2-0.3	6309
0.3-0.4	15049
0.4-0.5	9025
0.5-0.6	6624
0.6-0.7	2898
0.7-0.8	289
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC72755
0.875	High Similarity	NPC476367
0.8625	High Similarity	NPC52755
0.8523	High Similarity	NPC119379
0.8444	Intermediate Similarity	NPC103165
0.8444	Intermediate Similarity	NPC210717
0.8295	Intermediate Similarity	NPC191323
0.8202	Intermediate Similarity	NPC114389
0.8171	Intermediate Similarity	NPC137587
0.8161	Intermediate Similarity	NPC476948
0.8152	Intermediate Similarity	NPC261807
0.8152	Intermediate Similarity	NPC474994
0.8152	Intermediate Similarity	NPC476040
0.8152	Intermediate Similarity	NPC476021
0.8148	Intermediate Similarity	NPC63958
0.809	Intermediate Similarity	NPC261990
0.809	Intermediate Similarity	NPC474249
0.8068	Intermediate Similarity	NPC473436
0.8052	Intermediate Similarity	NPC117607
0.8052	Intermediate Similarity	NPC101307
0.8052	Intermediate Similarity	NPC88454
0.8049	Intermediate Similarity	NPC169994
0.8025	Intermediate Similarity	NPC472952
0.8025	Intermediate Similarity	NPC472950
0.8023	Intermediate Similarity	NPC86238
0.8	Intermediate Similarity	NPC275671
0.7976	Intermediate Similarity	NPC16449
0.7975	Intermediate Similarity	NPC283316
0.7912	Intermediate Similarity	NPC137461
0.7882	Intermediate Similarity	NPC249423
0.7849	Intermediate Similarity	NPC72204
0.7848	Intermediate Similarity	NPC9942
0.7848	Intermediate Similarity	NPC210323
0.7841	Intermediate Similarity	NPC255143
0.7841	Intermediate Similarity	NPC125399
0.7802	Intermediate Similarity	NPC289361
0.7778	Intermediate Similarity	NPC128066
0.7778	Intermediate Similarity	NPC95165
0.7778	Intermediate Similarity	NPC115607
0.7765	Intermediate Similarity	NPC471266
0.7765	Intermediate Similarity	NPC95124
0.7753	Intermediate Similarity	NPC189777
0.7742	Intermediate Similarity	NPC8774
0.7727	Intermediate Similarity	NPC164424
0.7727	Intermediate Similarity	NPC470360
0.7722	Intermediate Similarity	NPC245795
0.7722	Intermediate Similarity	NPC244790
0.7722	Intermediate Similarity	NPC2648
0.7722	Intermediate Similarity	NPC266578
0.7717	Intermediate Similarity	NPC27531
0.7711	Intermediate Similarity	NPC470766
0.7701	Intermediate Similarity	NPC211135
0.7701	Intermediate Similarity	NPC216420
0.7701	Intermediate Similarity	NPC85095
0.7692	Intermediate Similarity	NPC11216
0.7692	Intermediate Similarity	NPC291484
0.7692	Intermediate Similarity	NPC3345
0.7692	Intermediate Similarity	NPC80561
0.7692	Intermediate Similarity	NPC329596
0.7692	Intermediate Similarity	NPC204188
0.7683	Intermediate Similarity	NPC470151
0.7674	Intermediate Similarity	NPC471270
0.7667	Intermediate Similarity	NPC133588
0.766	Intermediate Similarity	NPC306797
0.766	Intermediate Similarity	NPC90583
0.766	Intermediate Similarity	NPC292718
0.766	Intermediate Similarity	NPC227583
0.766	Intermediate Similarity	NPC98457
0.766	Intermediate Similarity	NPC12103
0.766	Intermediate Similarity	NPC288970
0.766	Intermediate Similarity	NPC169270
0.766	Intermediate Similarity	NPC111834
0.764	Intermediate Similarity	NPC299068
0.764	Intermediate Similarity	NPC71520
0.764	Intermediate Similarity	NPC269058
0.7634	Intermediate Similarity	NPC144202
0.7634	Intermediate Similarity	NPC65402
0.7634	Intermediate Similarity	NPC127718
0.7625	Intermediate Similarity	NPC234511
0.7614	Intermediate Similarity	NPC15534
0.7609	Intermediate Similarity	NPC97404
0.7609	Intermediate Similarity	NPC91251
0.7609	Intermediate Similarity	NPC41554
0.7609	Intermediate Similarity	NPC219516
0.7609	Intermediate Similarity	NPC210268
0.7595	Intermediate Similarity	NPC253303
0.7595	Intermediate Similarity	NPC269077
0.759	Intermediate Similarity	NPC32832
0.7586	Intermediate Similarity	NPC259858
0.7586	Intermediate Similarity	NPC155521
0.7586	Intermediate Similarity	NPC471408
0.7582	Intermediate Similarity	NPC187785
0.7582	Intermediate Similarity	NPC259875
0.7582	Intermediate Similarity	NPC59682
0.7582	Intermediate Similarity	NPC161560
0.7582	Intermediate Similarity	NPC97103
0.7582	Intermediate Similarity	NPC470361
0.7582	Intermediate Similarity	NPC109744
0.7579	Intermediate Similarity	NPC316604
0.7558	Intermediate Similarity	NPC472951
0.7558	Intermediate Similarity	NPC186588
0.7558	Intermediate Similarity	NPC236707
0.7558	Intermediate Similarity	NPC287749
0.7558	Intermediate Similarity	NPC472943
0.7556	Intermediate Similarity	NPC233744
0.7553	Intermediate Similarity	NPC241047
0.7529	Intermediate Similarity	NPC31828
0.7529	Intermediate Similarity	NPC148977
0.7528	Intermediate Similarity	NPC290731
0.7527	Intermediate Similarity	NPC296620
0.7526	Intermediate Similarity	NPC235920
0.7526	Intermediate Similarity	NPC96784
0.7526	Intermediate Similarity	NPC476896
0.75	Intermediate Similarity	NPC477875
0.75	Intermediate Similarity	NPC10274
0.75	Intermediate Similarity	NPC276616
0.75	Intermediate Similarity	NPC312325
0.75	Intermediate Similarity	NPC185605
0.75	Intermediate Similarity	NPC477876
0.75	Intermediate Similarity	NPC473956
0.75	Intermediate Similarity	NPC102426
0.75	Intermediate Similarity	NPC475751
0.75	Intermediate Similarity	NPC300179
0.75	Intermediate Similarity	NPC265588
0.7474	Intermediate Similarity	NPC471903
0.7471	Intermediate Similarity	NPC476646
0.747	Intermediate Similarity	NPC306727
0.747	Intermediate Similarity	NPC476366
0.747	Intermediate Similarity	NPC201048
0.7468	Intermediate Similarity	NPC476406
0.7449	Intermediate Similarity	NPC214277
0.7447	Intermediate Similarity	NPC305160
0.7444	Intermediate Similarity	NPC476217
0.7444	Intermediate Similarity	NPC94462
0.7444	Intermediate Similarity	NPC121981
0.7442	Intermediate Similarity	NPC476316
0.7439	Intermediate Similarity	NPC167706
0.7439	Intermediate Similarity	NPC471268
0.7439	Intermediate Similarity	NPC471271
0.7423	Intermediate Similarity	NPC79303
0.7423	Intermediate Similarity	NPC38855
0.7416	Intermediate Similarity	NPC83702
0.7416	Intermediate Similarity	NPC474047
0.7412	Intermediate Similarity	NPC130136
0.7412	Intermediate Similarity	NPC471798
0.7412	Intermediate Similarity	NPC470711
0.7412	Intermediate Similarity	NPC470758
0.7407	Intermediate Similarity	NPC470833
0.7396	Intermediate Similarity	NPC274793
0.7396	Intermediate Similarity	NPC240372
0.7396	Intermediate Similarity	NPC477226
0.7391	Intermediate Similarity	NPC138974
0.7391	Intermediate Similarity	NPC49783
0.7391	Intermediate Similarity	NPC74258
0.7386	Intermediate Similarity	NPC477446
0.7386	Intermediate Similarity	NPC470155
0.7386	Intermediate Similarity	NPC477447
0.7381	Intermediate Similarity	NPC103822
0.7368	Intermediate Similarity	NPC30477
0.7368	Intermediate Similarity	NPC473348
0.7363	Intermediate Similarity	NPC44538
0.7363	Intermediate Similarity	NPC186145
0.7363	Intermediate Similarity	NPC477600
0.7363	Intermediate Similarity	NPC304083
0.7363	Intermediate Similarity	NPC245004
0.7363	Intermediate Similarity	NPC474657
0.7356	Intermediate Similarity	NPC96362
0.7353	Intermediate Similarity	NPC305939
0.7353	Intermediate Similarity	NPC154906
0.7347	Intermediate Similarity	NPC289670
0.7347	Intermediate Similarity	NPC49532
0.7342	Intermediate Similarity	NPC258595
0.734	Intermediate Similarity	NPC310013
0.7333	Intermediate Similarity	NPC471267
0.7326	Intermediate Similarity	NPC472342
0.7326	Intermediate Similarity	NPC472501
0.7326	Intermediate Similarity	NPC472500
0.7326	Intermediate Similarity	NPC471769
0.7326	Intermediate Similarity	NPC472499
0.7326	Intermediate Similarity	NPC167891
0.7326	Intermediate Similarity	NPC476314
0.7326	Intermediate Similarity	NPC11908
0.7326	Intermediate Similarity	NPC83351
0.732	Intermediate Similarity	NPC247233
0.732	Intermediate Similarity	NPC476895
0.732	Intermediate Similarity	NPC469725
0.7312	Intermediate Similarity	NPC123252
0.7312	Intermediate Similarity	NPC219937
0.7312	Intermediate Similarity	NPC194485
0.7312	Intermediate Similarity	NPC53890
0.7312	Intermediate Similarity	NPC295668
0.7303	Intermediate Similarity	NPC241959
0.7303	Intermediate Similarity	NPC82623
0.7303	Intermediate Similarity	NPC113978
0.7294	Intermediate Similarity	NPC253190
0.7294	Intermediate Similarity	NPC470749
0.7294	Intermediate Similarity	NPC91573
0.7294	Intermediate Similarity	NPC470145
0.7294	Intermediate Similarity	NPC329626
0.7283	Intermediate Similarity	NPC476379

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 NPC477978 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	2692
0.2-0.3	3874
0.3-0.4	1644
0.4-0.5	434
0.5-0.6	246
0.6-0.7	45
0.7-0.8	2
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
0.7556	Intermediate Similarity	NPD7524	Approved
0.7255	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD371	Approved
0.7172	Intermediate Similarity	NPD5344	Discontinued
0.7111	Intermediate Similarity	NPD6695	Phase 3
0.7045	Intermediate Similarity	NPD7645	Phase 2
0.7033	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6931	Approved
0.6966	Remote Similarity	NPD6930	Phase 2
0.6857	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6929	Approved
0.6832	Remote Similarity	NPD4159	Approved
0.6809	Remote Similarity	NPD7750	Discontinued
0.6786	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7514	Phase 3
0.6778	Remote Similarity	NPD7525	Registered
0.6778	Remote Similarity	NPD7332	Phase 2
0.6742	Remote Similarity	NPD7145	Approved
0.6733	Remote Similarity	NPD6648	Approved
0.6703	Remote Similarity	NPD6902	Approved
0.6629	Remote Similarity	NPD6932	Approved
0.6629	Remote Similarity	NPD6925	Approved
0.6629	Remote Similarity	NPD5776	Phase 2
0.6598	Remote Similarity	NPD3168	Discontinued
0.6596	Remote Similarity	NPD6893	Approved
0.6569	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7640	Approved
0.6531	Remote Similarity	NPD7087	Discontinued
0.6522	Remote Similarity	NPD6898	Phase 1
0.6517	Remote Similarity	NPD6933	Approved
0.6491	Remote Similarity	NPD6921	Approved
0.6481	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD7638	Approved
0.646	Remote Similarity	NPD7516	Approved
0.6458	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7115	Discovery
0.6404	Remote Similarity	NPD6942	Approved
0.6404	Remote Similarity	NPD8264	Approved
0.6404	Remote Similarity	NPD7339	Approved
0.6372	Remote Similarity	NPD7328	Approved
0.6372	Remote Similarity	NPD7327	Approved
0.6333	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6683	Phase 2
0.6292	Remote Similarity	NPD6924	Approved
0.6292	Remote Similarity	NPD6926	Approved
0.6239	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8378	Approved
0.6207	Remote Similarity	NPD8296	Approved
0.6207	Remote Similarity	NPD8380	Approved
0.6207	Remote Similarity	NPD8335	Approved
0.6207	Remote Similarity	NPD8379	Approved
0.6204	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7637	Suspended
0.6196	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8133	Approved
0.6132	Remote Similarity	NPD7632	Discontinued
0.6121	Remote Similarity	NPD8377	Approved
0.6121	Remote Similarity	NPD8294	Approved
0.6111	Remote Similarity	NPD5357	Phase 1
0.6082	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD8033	Approved
0.6068	Remote Similarity	NPD7503	Approved
0.6067	Remote Similarity	NPD7150	Approved
0.6067	Remote Similarity	NPD7152	Approved
0.6067	Remote Similarity	NPD7151	Approved
0.6064	Remote Similarity	NPD7509	Discontinued
0.6064	Remote Similarity	NPD6928	Phase 2
0.6055	Remote Similarity	NPD6412	Phase 2
0.604	Remote Similarity	NPD6079	Approved
0.602	Remote Similarity	NPD3618	Phase 1
0.6018	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD5328	Approved
0.5983	Remote Similarity	NPD6054	Approved
0.5983	Remote Similarity	NPD6319	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.598	Remote Similarity	NPD8171	Discontinued
0.5979	Remote Similarity	NPD4786	Approved
0.5963	Remote Similarity	NPD6640	Phase 3
0.5955	Remote Similarity	NPD4787	Phase 1
0.5955	Remote Similarity	NPD7143	Approved
0.5955	Remote Similarity	NPD7144	Approved
0.5941	Remote Similarity	NPD7136	Phase 2
0.5941	Remote Similarity	NPD7838	Discovery
0.5938	Remote Similarity	NPD3667	Approved
0.5934	Remote Similarity	NPD4784	Approved
0.5934	Remote Similarity	NPD4785	Approved
0.5934	Remote Similarity	NPD1811	Approved
0.5934	Remote Similarity	NPD1810	Approved
0.5929	Remote Similarity	NPD8297	Approved
0.5922	Remote Similarity	NPD7748	Approved
0.5895	Remote Similarity	NPD4748	Discontinued
0.5893	Remote Similarity	NPD4634	Approved
0.5889	Remote Similarity	NPD4243	Approved
0.5882	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD8035	Phase 2
0.5882	Remote Similarity	NPD8034	Phase 2
0.5882	Remote Similarity	NPD7515	Phase 2
0.5872	Remote Similarity	NPD5141	Approved
0.587	Remote Similarity	NPD3703	Phase 2
0.5868	Remote Similarity	NPD7507	Approved
0.5856	Remote Similarity	NPD6881	Approved
0.5856	Remote Similarity	NPD6899	Approved
0.5854	Remote Similarity	NPD7319	Approved
0.5851	Remote Similarity	NPD6697	Approved
0.5851	Remote Similarity	NPD6118	Approved
0.5851	Remote Similarity	NPD6114	Approved
0.5851	Remote Similarity	NPD6115	Approved
0.5847	Remote Similarity	NPD6059	Approved
0.5843	Remote Similarity	NPD6922	Approved
0.5843	Remote Similarity	NPD6923	Approved
0.5833	Remote Similarity	NPD7604	Phase 2
0.5825	Remote Similarity	NPD5778	Approved
0.5825	Remote Similarity	NPD4202	Approved
0.5825	Remote Similarity	NPD5779	Approved
0.5824	Remote Similarity	NPD4732	Discontinued
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.5798	Remote Similarity	NPD6015	Approved
0.5798	Remote Similarity	NPD6016	Approved
0.5794	Remote Similarity	NPD5286	Approved
0.5794	Remote Similarity	NPD4696	Approved
0.5794	Remote Similarity	NPD5285	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.5784	Remote Similarity	NPD46	Approved
0.5784	Remote Similarity	NPD6698	Approved
0.5766	Remote Similarity	NPD5697	Approved
0.5765	Remote Similarity	NPD368	Approved
0.5755	Remote Similarity	NPD4755	Approved
0.5755	Remote Similarity	NPD7902	Approved
0.5752	Remote Similarity	NPD7102	Approved
0.5752	Remote Similarity	NPD6883	Approved
0.5752	Remote Similarity	NPD7290	Approved
0.575	Remote Similarity	NPD5988	Approved
0.5738	Remote Similarity	NPD6616	Approved
0.5726	Remote Similarity	NPD6009	Approved
0.5726	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4788	Approved
0.5714	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD6649	Approved
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6650	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD8328	Phase 3
0.5702	Remote Similarity	NPD6869	Approved
0.5691	Remote Similarity	NPD7078	Approved
0.5688	Remote Similarity	NPD5226	Approved
0.5688	Remote Similarity	NPD4633	Approved
0.5688	Remote Similarity	NPD5225	Approved
0.5688	Remote Similarity	NPD5224	Approved
0.5676	Remote Similarity	NPD6008	Approved
0.5673	Remote Similarity	NPD6399	Phase 3
0.5667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5983	Phase 2
0.5664	Remote Similarity	NPD6012	Approved
0.5664	Remote Similarity	NPD6372	Approved
0.5664	Remote Similarity	NPD6373	Approved
0.5664	Remote Similarity	NPD6013	Approved
0.5664	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD5221	Approved
0.566	Remote Similarity	NPD5222	Approved
0.566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3133	Approved
0.5657	Remote Similarity	NPD3665	Phase 1
0.5657	Remote Similarity	NPD3666	Approved
0.5652	Remote Similarity	NPD6882	Approved
0.5648	Remote Similarity	NPD4700	Approved
0.5647	Remote Similarity	NPD1145	Discontinued
0.5645	Remote Similarity	NPD7736	Approved
0.5641	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6117	Approved
0.5636	Remote Similarity	NPD5175	Approved
0.5636	Remote Similarity	NPD5174	Approved
0.5625	Remote Similarity	NPD5701	Approved
0.5625	Remote Similarity	NPD4195	Approved
0.561	Remote Similarity	NPD6336	Discontinued
0.5607	Remote Similarity	NPD5173	Approved
0.5607	Remote Similarity	NPD6083	Phase 2
0.5607	Remote Similarity	NPD6084	Phase 2
0.5604	Remote Similarity	NPD2687	Approved
0.5604	Remote Similarity	NPD2254	Approved
0.5604	Remote Similarity	NPD2686	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