NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.17
Volume:	289.511
LogP:	2.592
LogD:	2.556
LogS:	-3.396
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	4.86
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.647
MDCK Permeability:	3.626067336881533e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.571

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.951
Plasma Protein Binding (PPB):	73.52215576171875%
Volume Distribution (VD):	1.099
Pgp-substrate:	34.09971237182617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.767
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	12.336
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.49
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.462
Rat Oral Acute Toxicity:	0.326
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.845
Carcinogencity:	0.623
Eye Corrosion:	0.493
Eye Irritation:	0.837
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC248574

Natural Product ID:	NPC248574
*Common Name:**	Oblongolide X
IUPAC Name:	(2S,4aS,6aR,8S,10aS,10bR)-2-hydroxy-2-(hydroxymethyl)-8,10b-dimethyl-4,4a,6a,7,8,9,10,10a-octahydrobenzo[f]isochromen-1-one
Synonyms:	Oblongolide X
Standard InCHIKey:	ALFVRDAMPYOPQO-VHPSDLRFSA-N
Standard InCHI:	InChI=1S/C16H24O4/c1-10-3-6-13-11(7-10)4-5-12-8-20-16(19,9-17)14(18)15(12,13)2/h4-5,10-13,17,19H,3,6-9H2,1-2H3/t10-,11-,12+,13-,15-,16-/m0/s1
SMILES:	OC[C@]1(O)OC[C@@H]2[C@@](C1=O)(C)[C@H]1CC[C@@H](C[C@@H]1C=C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087551
PubChem CID:	44627606
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO33230	Phomopsis sp. BCC 9789	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038128]

☑ 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
MIC	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	96000.0	nM	PMID[452073]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	71000.0	nM	PMID[452073]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	71000.0	nM	PMID[452073]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	178000.0	nM	PMID[452073]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	>	178000.0	nM	PMID[452073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	71000.0	nM	PMID[452073]

☑ 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 NPC248574 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	204
0.1-0.2	1272
0.2-0.3	4516
0.3-0.4	10090
0.4-0.5	12636
0.5-0.6	6941
0.6-0.7	5818
0.7-0.8	1206
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.967	High Similarity	NPC469565
0.9205	High Similarity	NPC230016
0.8632	High Similarity	NPC469528
0.8632	High Similarity	NPC469369
0.7925	Intermediate Similarity	NPC471243
0.7917	Intermediate Similarity	NPC214844
0.7905	Intermediate Similarity	NPC87335
0.785	Intermediate Similarity	NPC205534
0.7849	Intermediate Similarity	NPC469569
0.7843	Intermediate Similarity	NPC478176
0.7835	Intermediate Similarity	NPC324157
0.7826	Intermediate Similarity	NPC212083
0.7822	Intermediate Similarity	NPC472972
0.7818	Intermediate Similarity	NPC297179
0.7778	Intermediate Similarity	NPC320118
0.7778	Intermediate Similarity	NPC194273
0.7778	Intermediate Similarity	NPC108141
0.7757	Intermediate Similarity	NPC201992
0.7748	Intermediate Similarity	NPC469488
0.7748	Intermediate Similarity	NPC319570
0.7732	Intermediate Similarity	NPC15059
0.7723	Intermediate Similarity	NPC70733
0.7723	Intermediate Similarity	NPC56071
0.7717	Intermediate Similarity	NPC14151
0.7714	Intermediate Similarity	NPC144854
0.7714	Intermediate Similarity	NPC293512
0.7714	Intermediate Similarity	NPC3316
0.7706	Intermediate Similarity	NPC243354
0.7706	Intermediate Similarity	NPC474906
0.7706	Intermediate Similarity	NPC18547
0.7692	Intermediate Similarity	NPC160843
0.7685	Intermediate Similarity	NPC289312
0.7685	Intermediate Similarity	NPC11252
0.7685	Intermediate Similarity	NPC130427
0.7684	Intermediate Similarity	NPC94666
0.7658	Intermediate Similarity	NPC204552
0.7658	Intermediate Similarity	NPC188667
0.7658	Intermediate Similarity	NPC17772
0.7658	Intermediate Similarity	NPC286347
0.7642	Intermediate Similarity	NPC192813
0.7642	Intermediate Similarity	NPC277017
0.7642	Intermediate Similarity	NPC154608
0.7642	Intermediate Similarity	NPC293850
0.7636	Intermediate Similarity	NPC473126
0.7636	Intermediate Similarity	NPC235539
0.7636	Intermediate Similarity	NPC134869
0.7636	Intermediate Similarity	NPC152199
0.7629	Intermediate Similarity	NPC474700
0.7624	Intermediate Similarity	NPC124246
0.7624	Intermediate Similarity	NPC278506
0.7624	Intermediate Similarity	NPC27105
0.7619	Intermediate Similarity	NPC166607
0.7619	Intermediate Similarity	NPC210178
0.7615	Intermediate Similarity	NPC198539
0.7615	Intermediate Similarity	NPC7921
0.7615	Intermediate Similarity	NPC477266
0.7615	Intermediate Similarity	NPC51978
0.7615	Intermediate Similarity	NPC208998
0.7611	Intermediate Similarity	NPC102822
0.7611	Intermediate Similarity	NPC75417
0.7611	Intermediate Similarity	NPC477046
0.7604	Intermediate Similarity	NPC298904
0.7596	Intermediate Similarity	NPC131366
0.7596	Intermediate Similarity	NPC275583
0.7593	Intermediate Similarity	NPC317107
0.7593	Intermediate Similarity	NPC171888
0.7593	Intermediate Similarity	NPC146945
0.7589	Intermediate Similarity	NPC11551
0.7589	Intermediate Similarity	NPC472949
0.7589	Intermediate Similarity	NPC114441
0.7589	Intermediate Similarity	NPC208381
0.7589	Intermediate Similarity	NPC473884
0.7589	Intermediate Similarity	NPC39211
0.7589	Intermediate Similarity	NPC180550
0.7589	Intermediate Similarity	NPC475171
0.7589	Intermediate Similarity	NPC214484
0.7589	Intermediate Similarity	NPC309780
0.7589	Intermediate Similarity	NPC469945
0.7589	Intermediate Similarity	NPC6377
0.7589	Intermediate Similarity	NPC157868
0.7589	Intermediate Similarity	NPC35405
0.7579	Intermediate Similarity	NPC263997
0.7579	Intermediate Similarity	NPC241512
0.7579	Intermediate Similarity	NPC8518
0.7579	Intermediate Similarity	NPC79573
0.7579	Intermediate Similarity	NPC132228
0.7579	Intermediate Similarity	NPC6185
0.7576	Intermediate Similarity	NPC478037
0.7576	Intermediate Similarity	NPC478036
0.757	Intermediate Similarity	NPC218853
0.757	Intermediate Similarity	NPC141350
0.757	Intermediate Similarity	NPC246205
0.757	Intermediate Similarity	NPC250018
0.757	Intermediate Similarity	NPC27814
0.7568	Intermediate Similarity	NPC97908
0.7568	Intermediate Similarity	NPC122033
0.7568	Intermediate Similarity	NPC218970
0.7568	Intermediate Similarity	NPC27999
0.7568	Intermediate Similarity	NPC477116
0.7568	Intermediate Similarity	NPC470854
0.7568	Intermediate Similarity	NPC474654
0.7568	Intermediate Similarity	NPC287343
0.7568	Intermediate Similarity	NPC224121
0.7549	Intermediate Similarity	NPC203388
0.7549	Intermediate Similarity	NPC471331
0.7549	Intermediate Similarity	NPC472687
0.7549	Intermediate Similarity	NPC99657
0.7549	Intermediate Similarity	NPC471330
0.7547	Intermediate Similarity	NPC202524
0.7545	Intermediate Similarity	NPC469877
0.7545	Intermediate Similarity	NPC247069
0.7545	Intermediate Similarity	NPC470919
0.7545	Intermediate Similarity	NPC474557
0.7544	Intermediate Similarity	NPC471965
0.7544	Intermediate Similarity	NPC162574
0.7544	Intermediate Similarity	NPC275343
0.7527	Intermediate Similarity	NPC116797
0.7526	Intermediate Similarity	NPC1753
0.7526	Intermediate Similarity	NPC474511
0.7525	Intermediate Similarity	NPC472733
0.7525	Intermediate Similarity	NPC472734
0.7524	Intermediate Similarity	NPC255309
0.7524	Intermediate Similarity	NPC100955
0.7524	Intermediate Similarity	NPC121566
0.7523	Intermediate Similarity	NPC302146
0.7523	Intermediate Similarity	NPC317687
0.7522	Intermediate Similarity	NPC112038
0.7522	Intermediate Similarity	NPC294112
0.75	Intermediate Similarity	NPC474963
0.75	Intermediate Similarity	NPC324063
0.75	Intermediate Similarity	NPC475317
0.75	Intermediate Similarity	NPC477054
0.75	Intermediate Similarity	NPC470776
0.75	Intermediate Similarity	NPC251310
0.75	Intermediate Similarity	NPC475632
0.75	Intermediate Similarity	NPC225049
0.75	Intermediate Similarity	NPC52241
0.75	Intermediate Similarity	NPC86020
0.75	Intermediate Similarity	NPC476126
0.75	Intermediate Similarity	NPC109588
0.75	Intermediate Similarity	NPC210005
0.75	Intermediate Similarity	NPC476235
0.75	Intermediate Similarity	NPC154856
0.75	Intermediate Similarity	NPC474567
0.75	Intermediate Similarity	NPC181066
0.75	Intermediate Similarity	NPC469947
0.75	Intermediate Similarity	NPC474113
0.7478	Intermediate Similarity	NPC471964
0.7478	Intermediate Similarity	NPC14617
0.7478	Intermediate Similarity	NPC238005
0.7478	Intermediate Similarity	NPC202666
0.7478	Intermediate Similarity	NPC262199
0.7478	Intermediate Similarity	NPC141196
0.7478	Intermediate Similarity	NPC471961
0.7478	Intermediate Similarity	NPC1980
0.7477	Intermediate Similarity	NPC40632
0.7477	Intermediate Similarity	NPC259306
0.7477	Intermediate Similarity	NPC473288
0.7477	Intermediate Similarity	NPC31797
0.7477	Intermediate Similarity	NPC328374
0.7477	Intermediate Similarity	NPC470628
0.7477	Intermediate Similarity	NPC251236
0.7477	Intermediate Similarity	NPC474046
0.7477	Intermediate Similarity	NPC207217
0.7477	Intermediate Similarity	NPC272576
0.7477	Intermediate Similarity	NPC295389
0.7477	Intermediate Similarity	NPC96312
0.7476	Intermediate Similarity	NPC473576
0.7476	Intermediate Similarity	NPC167974
0.7476	Intermediate Similarity	NPC475156
0.7475	Intermediate Similarity	NPC26865
0.7456	Intermediate Similarity	NPC114484
0.7456	Intermediate Similarity	NPC86222
0.7456	Intermediate Similarity	NPC11242
0.7456	Intermediate Similarity	NPC159309
0.7456	Intermediate Similarity	NPC171544
0.7456	Intermediate Similarity	NPC301449
0.7456	Intermediate Similarity	NPC104372
0.7456	Intermediate Similarity	NPC242840
0.7456	Intermediate Similarity	NPC31838
0.7456	Intermediate Similarity	NPC223301
0.7456	Intermediate Similarity	NPC64715
0.7456	Intermediate Similarity	NPC31193
0.7456	Intermediate Similarity	NPC297263
0.7456	Intermediate Similarity	NPC22956
0.7456	Intermediate Similarity	NPC222580
0.7456	Intermediate Similarity	NPC62725
0.7455	Intermediate Similarity	NPC49451
0.7453	Intermediate Similarity	NPC95243
0.7453	Intermediate Similarity	NPC96377
0.7453	Intermediate Similarity	NPC471332
0.7453	Intermediate Similarity	NPC102352
0.7453	Intermediate Similarity	NPC162033
0.7453	Intermediate Similarity	NPC63023
0.7453	Intermediate Similarity	NPC292588
0.7453	Intermediate Similarity	NPC471333
0.7451	Intermediate Similarity	NPC473161
0.7451	Intermediate Similarity	NPC472732
0.7451	Intermediate Similarity	NPC272451
0.7451	Intermediate Similarity	NPC472731

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 NPC248574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1600
0.2-0.3	3834
0.3-0.4	2328
0.4-0.5	718
0.5-0.6	247
0.6-0.7	203
0.7-0.8	36
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
0.7547	Intermediate Similarity	NPD6412	Phase 2
0.7478	Intermediate Similarity	NPD8328	Phase 3
0.7411	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6054	Approved
0.7315	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6016	Approved
0.7304	Intermediate Similarity	NPD6015	Approved
0.73	Intermediate Similarity	NPD6411	Approved
0.7282	Intermediate Similarity	NPD6083	Phase 2
0.7282	Intermediate Similarity	NPD6084	Phase 2
0.7263	Intermediate Similarity	NPD3667	Approved
0.7255	Intermediate Similarity	NPD5695	Phase 3
0.7241	Intermediate Similarity	NPD6370	Approved
0.7241	Intermediate Similarity	NPD5988	Approved
0.7234	Intermediate Similarity	NPD4695	Discontinued
0.7228	Intermediate Similarity	NPD6399	Phase 3
0.7217	Intermediate Similarity	NPD6059	Approved
0.7217	Intermediate Similarity	NPD6319	Approved
0.7212	Intermediate Similarity	NPD5696	Approved
0.7172	Intermediate Similarity	NPD6672	Approved
0.7172	Intermediate Similarity	NPD5737	Approved
0.7157	Intermediate Similarity	NPD5282	Discontinued
0.7119	Intermediate Similarity	NPD7492	Approved
0.7113	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD6009	Approved
0.71	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4753	Phase 2
0.7091	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5210	Approved
0.7087	Intermediate Similarity	NPD4629	Approved
0.7059	Intermediate Similarity	NPD6616	Approved
0.7027	Intermediate Similarity	NPD4634	Approved
0.7	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD6686	Approved
0.6991	Remote Similarity	NPD4632	Approved
0.697	Remote Similarity	NPD5279	Phase 3
0.697	Remote Similarity	NPD3618	Phase 1
0.6957	Remote Similarity	NPD7115	Discovery
0.6942	Remote Similarity	NPD7736	Approved
0.6939	Remote Similarity	NPD3133	Approved
0.6939	Remote Similarity	NPD3666	Approved
0.6939	Remote Similarity	NPD3665	Phase 1
0.6909	Remote Similarity	NPD5697	Approved
0.6903	Remote Similarity	NPD8297	Approved
0.6903	Remote Similarity	NPD6882	Approved
0.6893	Remote Similarity	NPD5779	Approved
0.6893	Remote Similarity	NPD5778	Approved
0.686	Remote Similarity	NPD8293	Discontinued
0.6857	Remote Similarity	NPD5221	Approved
0.6857	Remote Similarity	NPD4697	Phase 3
0.6857	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5222	Approved
0.6847	Remote Similarity	NPD6899	Approved
0.6847	Remote Similarity	NPD6881	Approved
0.6847	Remote Similarity	NPD6011	Approved
0.6829	Remote Similarity	NPD5956	Approved
0.6827	Remote Similarity	NPD7748	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD6649	Approved
0.6814	Remote Similarity	NPD6650	Approved
0.6803	Remote Similarity	NPD6033	Approved
0.68	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5690	Phase 2
0.68	Remote Similarity	NPD6098	Approved
0.6796	Remote Similarity	NPD7515	Phase 2
0.6796	Remote Similarity	NPD5694	Approved
0.6792	Remote Similarity	NPD7902	Approved
0.6792	Remote Similarity	NPD5173	Approved
0.6786	Remote Similarity	NPD6012	Approved
0.6786	Remote Similarity	NPD6013	Approved
0.6786	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD6014	Approved
0.6786	Remote Similarity	NPD6373	Approved
0.6768	Remote Similarity	NPD3668	Phase 3
0.6768	Remote Similarity	NPD4197	Approved
0.6765	Remote Similarity	NPD6673	Approved
0.6765	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6080	Approved
0.6765	Remote Similarity	NPD6904	Approved
0.6757	Remote Similarity	NPD5701	Approved
0.6729	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD7102	Approved
0.6726	Remote Similarity	NPD7290	Approved
0.6726	Remote Similarity	NPD6883	Approved
0.6723	Remote Similarity	NPD5983	Phase 2
0.67	Remote Similarity	NPD5329	Approved
0.6699	Remote Similarity	NPD5692	Phase 3
0.6696	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD4755	Approved
0.6635	Remote Similarity	NPD5693	Phase 1
0.6635	Remote Similarity	NPD5284	Approved
0.6635	Remote Similarity	NPD5281	Approved
0.6635	Remote Similarity	NPD6079	Approved
0.6635	Remote Similarity	NPD6050	Approved
0.6634	Remote Similarity	NPD5330	Approved
0.6634	Remote Similarity	NPD7146	Approved
0.6634	Remote Similarity	NPD6409	Approved
0.6634	Remote Similarity	NPD6684	Approved
0.6634	Remote Similarity	NPD7521	Approved
0.6634	Remote Similarity	NPD5280	Approved
0.6634	Remote Similarity	NPD4694	Approved
0.6634	Remote Similarity	NPD7334	Approved
0.6633	Remote Similarity	NPD5369	Approved
0.6612	Remote Similarity	NPD7604	Phase 2
0.6606	Remote Similarity	NPD5223	Approved
0.6602	Remote Similarity	NPD5328	Approved
0.6583	Remote Similarity	NPD6921	Approved
0.6569	Remote Similarity	NPD3573	Approved
0.6566	Remote Similarity	NPD4223	Phase 3
0.6566	Remote Similarity	NPD4221	Approved
0.6555	Remote Similarity	NPD4522	Approved
0.6545	Remote Similarity	NPD5226	Approved
0.6545	Remote Similarity	NPD5225	Approved
0.6545	Remote Similarity	NPD5224	Approved
0.6545	Remote Similarity	NPD5211	Phase 2
0.6545	Remote Similarity	NPD4633	Approved
0.6522	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4700	Approved
0.6509	Remote Similarity	NPD7900	Approved
0.6509	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6903	Approved
0.6504	Remote Similarity	NPD6336	Discontinued
0.6486	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD5174	Approved
0.6476	Remote Similarity	NPD7637	Suspended
0.6476	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD4623	Approved
0.6471	Remote Similarity	NPD4519	Discontinued
0.6446	Remote Similarity	NPD8513	Phase 3
0.6446	Remote Similarity	NPD8515	Approved
0.6446	Remote Similarity	NPD8517	Approved
0.6446	Remote Similarity	NPD8516	Approved
0.6441	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD5141	Approved
0.6422	Remote Similarity	NPD7638	Approved
0.6415	Remote Similarity	NPD4202	Approved
0.64	Remote Similarity	NPD4269	Approved
0.64	Remote Similarity	NPD4270	Approved
0.6389	Remote Similarity	NPD7839	Suspended
0.6387	Remote Similarity	NPD6317	Approved
0.6381	Remote Similarity	NPD6698	Approved
0.6381	Remote Similarity	NPD5785	Approved
0.6381	Remote Similarity	NPD5207	Approved
0.6381	Remote Similarity	NPD46	Approved
0.6372	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7640	Approved
0.6349	Remote Similarity	NPD7319	Approved
0.6348	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6067	Discontinued
0.6339	Remote Similarity	NPD4754	Approved
0.6337	Remote Similarity	NPD6110	Phase 1
0.6333	Remote Similarity	NPD6313	Approved
0.6333	Remote Similarity	NPD6314	Approved
0.6333	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD4693	Phase 3
0.6311	Remote Similarity	NPD4138	Approved
0.6311	Remote Similarity	NPD5786	Approved
0.6311	Remote Similarity	NPD4688	Approved
0.6311	Remote Similarity	NPD4689	Approved
0.6311	Remote Similarity	NPD4690	Approved
0.6311	Remote Similarity	NPD5205	Approved
0.6303	Remote Similarity	NPD6274	Approved
0.6296	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5654	Approved
0.6296	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6371	Approved
0.6289	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7101	Approved
0.6281	Remote Similarity	NPD7100	Approved
0.6271	Remote Similarity	NPD8133	Approved
0.6261	Remote Similarity	NPD5168	Approved
0.6261	Remote Similarity	NPD4729	Approved
0.6261	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD5091	Approved
0.625	Remote Similarity	NPD7260	Phase 2
0.624	Remote Similarity	NPD7507	Approved
0.6238	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4767	Approved
0.6228	Remote Similarity	NPD4768	Approved
0.6214	Remote Similarity	NPD5363	Approved
0.6214	Remote Similarity	NPD1694	Approved
0.62	Remote Similarity	NPD4252	Approved
0.619	Remote Similarity	NPD5208	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