NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.17
Volume:	289.511
LogP:	2.868
LogD:	2.547
LogS:	-3.032
# 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:	0.564
Synthetic Accessibility Score:	4.784
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:	-4.86
MDCK Permeability:	4.0037113649304956e-05
Pgp-inhibitor:	0.384
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.301

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923
Plasma Protein Binding (PPB):	59.258445739746094%
Volume Distribution (VD):	0.71
Pgp-substrate:	25.56471824645996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.613
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.725
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.807
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	10.277
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.265
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.758
Carcinogencity:	0.801
Eye Corrosion:	0.263
Eye Irritation:	0.796
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC469528

Natural Product ID:	NPC469528
*Common Name:**	Oblongolide W1
IUPAC Name:	(1S,4aS,6aR,8S,10aS,10bR)-1-hydroxy-1-(hydroxymethyl)-8,10b-dimethyl-4,4a,6a,7,8,9,10,10a-octahydrobenzo[f]isochromen-2-one
Synonyms:	Oblongolide W1
Standard InCHIKey:	JDKSFOWBWOHISV-VHPSDLRFSA-N
Standard InCHI:	InChI=1S/C16H24O4/c1-10-3-6-13-11(7-10)4-5-12-8-20-14(18)16(19,9-17)15(12,13)2/h4-5,10-13,17,19H,3,6-9H2,1-2H3/t10-,11-,12+,13-,15-,16-/m0/s1
SMILES:	CC1CCC2C(C1)C=CC3C2(C(C(=O)OC3)(CO)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1084417
PubChem CID:	44627604
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	>	178000.0	nM	PMID[540213]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	71000.0	nM	PMID[540213]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	71000.0	nM	PMID[540213]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	178000.0	nM	PMID[540213]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	>	178000.0	nM	PMID[540213]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	71000.0	nM	PMID[540213]

☑ 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 NPC469528 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	211
0.1-0.2	1208
0.2-0.3	4324
0.3-0.4	8800
0.4-0.5	12771
0.5-0.6	7036
0.6-0.7	6026
0.7-0.8	2288
0.8-0.85	29
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469369
0.8632	High Similarity	NPC248574
0.8602	High Similarity	NPC214844
0.8381	Intermediate Similarity	NPC7921
0.8381	Intermediate Similarity	NPC208998
0.8367	Intermediate Similarity	NPC469565
0.8365	Intermediate Similarity	NPC171888
0.8365	Intermediate Similarity	NPC146945
0.8252	Intermediate Similarity	NPC293850
0.8211	Intermediate Similarity	NPC15059
0.8172	Intermediate Similarity	NPC262085
0.8165	Intermediate Similarity	NPC469488
0.8148	Intermediate Similarity	NPC470854
0.8148	Intermediate Similarity	NPC470775
0.8148	Intermediate Similarity	NPC97908
0.8148	Intermediate Similarity	NPC287343
0.8148	Intermediate Similarity	NPC176513
0.8148	Intermediate Similarity	NPC474654
0.8148	Intermediate Similarity	NPC122033
0.8137	Intermediate Similarity	NPC475036
0.8137	Intermediate Similarity	NPC258532
0.81	Intermediate Similarity	NPC167974
0.81	Intermediate Similarity	NPC472972
0.8095	Intermediate Similarity	NPC5103
0.8073	Intermediate Similarity	NPC188667
0.8073	Intermediate Similarity	NPC297179
0.8073	Intermediate Similarity	NPC470776
0.8073	Intermediate Similarity	NPC204552
0.8073	Intermediate Similarity	NPC17772
0.8073	Intermediate Similarity	NPC251310
0.8056	Intermediate Similarity	NPC207217
0.8037	Intermediate Similarity	NPC194100
0.8037	Intermediate Similarity	NPC49451
0.8019	Intermediate Similarity	NPC201992
0.8	Intermediate Similarity	NPC218853
0.7981	Intermediate Similarity	NPC3316
0.7981	Intermediate Similarity	NPC144854
0.7979	Intermediate Similarity	NPC324063
0.7963	Intermediate Similarity	NPC473898
0.7944	Intermediate Similarity	NPC302146
0.7944	Intermediate Similarity	NPC474516
0.7944	Intermediate Similarity	NPC11252
0.7944	Intermediate Similarity	NPC289312
0.7938	Intermediate Similarity	NPC36491
0.7928	Intermediate Similarity	NPC112038
0.7905	Intermediate Similarity	NPC154608
0.7905	Intermediate Similarity	NPC192813
0.7905	Intermediate Similarity	NPC289702
0.7905	Intermediate Similarity	NPC277017
0.7905	Intermediate Similarity	NPC208461
0.79	Intermediate Similarity	NPC124246
0.7895	Intermediate Similarity	NPC230016
0.789	Intermediate Similarity	NPC259306
0.789	Intermediate Similarity	NPC474734
0.789	Intermediate Similarity	NPC96312
0.789	Intermediate Similarity	NPC235539
0.789	Intermediate Similarity	NPC134869
0.789	Intermediate Similarity	NPC40632
0.789	Intermediate Similarity	NPC474046
0.789	Intermediate Similarity	NPC152199
0.789	Intermediate Similarity	NPC470628
0.789	Intermediate Similarity	NPC328374
0.789	Intermediate Similarity	NPC179626
0.789	Intermediate Similarity	NPC251236
0.7885	Intermediate Similarity	NPC475494
0.7872	Intermediate Similarity	NPC76333
0.787	Intermediate Similarity	NPC194273
0.787	Intermediate Similarity	NPC320118
0.787	Intermediate Similarity	NPC51978
0.787	Intermediate Similarity	NPC198539
0.787	Intermediate Similarity	NPC469496
0.787	Intermediate Similarity	NPC469463
0.787	Intermediate Similarity	NPC469454
0.7864	Intermediate Similarity	NPC4620
0.7857	Intermediate Similarity	NPC477046
0.7857	Intermediate Similarity	NPC102822
0.7857	Intermediate Similarity	NPC75417
0.785	Intermediate Similarity	NPC304180
0.785	Intermediate Similarity	NPC317107
0.785	Intermediate Similarity	NPC179798
0.785	Intermediate Similarity	NPC472003
0.7849	Intermediate Similarity	NPC476100
0.7838	Intermediate Similarity	NPC470777
0.783	Intermediate Similarity	NPC141350
0.783	Intermediate Similarity	NPC472534
0.783	Intermediate Similarity	NPC143706
0.7826	Intermediate Similarity	NPC327002
0.7818	Intermediate Similarity	NPC473590
0.781	Intermediate Similarity	NPC59530
0.781	Intermediate Similarity	NPC293512
0.7807	Intermediate Similarity	NPC473255
0.78	Intermediate Similarity	NPC269492
0.7798	Intermediate Similarity	NPC473798
0.7798	Intermediate Similarity	NPC18547
0.7798	Intermediate Similarity	NPC470919
0.7798	Intermediate Similarity	NPC116024
0.7798	Intermediate Similarity	NPC474906
0.7798	Intermediate Similarity	NPC469877
0.7798	Intermediate Similarity	NPC117712
0.7798	Intermediate Similarity	NPC243354
0.7789	Intermediate Similarity	NPC475753
0.7788	Intermediate Similarity	NPC284865
0.7788	Intermediate Similarity	NPC470104
0.7788	Intermediate Similarity	NPC296950
0.7788	Intermediate Similarity	NPC146731
0.7788	Intermediate Similarity	NPC475676
0.7788	Intermediate Similarity	NPC13385
0.7788	Intermediate Similarity	NPC220964
0.7778	Intermediate Similarity	NPC317687
0.7778	Intermediate Similarity	NPC90769
0.7767	Intermediate Similarity	NPC476126
0.7767	Intermediate Similarity	NPC476235
0.7767	Intermediate Similarity	NPC473788
0.7767	Intermediate Similarity	NPC475558
0.7767	Intermediate Similarity	NPC473928
0.7767	Intermediate Similarity	NPC473163
0.7757	Intermediate Similarity	NPC474567
0.7757	Intermediate Similarity	NPC210005
0.7757	Intermediate Similarity	NPC242611
0.7757	Intermediate Similarity	NPC250956
0.7748	Intermediate Similarity	NPC286347
0.7745	Intermediate Similarity	NPC35239
0.7745	Intermediate Similarity	NPC477656
0.7745	Intermediate Similarity	NPC477655
0.7736	Intermediate Similarity	NPC472218
0.7736	Intermediate Similarity	NPC472219
0.7736	Intermediate Similarity	NPC472217
0.7736	Intermediate Similarity	NPC295389
0.7732	Intermediate Similarity	NPC471342
0.7732	Intermediate Similarity	NPC469866
0.7732	Intermediate Similarity	NPC97577
0.7732	Intermediate Similarity	NPC471222
0.7732	Intermediate Similarity	NPC474700
0.7727	Intermediate Similarity	NPC270478
0.7723	Intermediate Similarity	NPC96597
0.7723	Intermediate Similarity	NPC91197
0.7723	Intermediate Similarity	NPC125551
0.7723	Intermediate Similarity	NPC309503
0.7723	Intermediate Similarity	NPC239547
0.7723	Intermediate Similarity	NPC155319
0.7719	Intermediate Similarity	NPC67251
0.7714	Intermediate Similarity	NPC477125
0.7714	Intermediate Similarity	NPC292588
0.7714	Intermediate Similarity	NPC162033
0.7714	Intermediate Similarity	NPC102352
0.7714	Intermediate Similarity	NPC477877
0.7714	Intermediate Similarity	NPC472655
0.7708	Intermediate Similarity	NPC477926
0.7706	Intermediate Similarity	NPC56448
0.7706	Intermediate Similarity	NPC477266
0.77	Intermediate Similarity	NPC286612
0.77	Intermediate Similarity	NPC230347
0.77	Intermediate Similarity	NPC322188
0.77	Intermediate Similarity	NPC275310
0.7692	Intermediate Similarity	NPC474330
0.7692	Intermediate Similarity	NPC321514
0.7692	Intermediate Similarity	NPC275583
0.7692	Intermediate Similarity	NPC474207
0.7692	Intermediate Similarity	NPC474165
0.7692	Intermediate Similarity	NPC69171
0.7685	Intermediate Similarity	NPC324683
0.7685	Intermediate Similarity	NPC31839
0.7685	Intermediate Similarity	NPC471243
0.7679	Intermediate Similarity	NPC473636
0.7679	Intermediate Similarity	NPC39211
0.7679	Intermediate Similarity	NPC35405
0.7679	Intermediate Similarity	NPC475171
0.7679	Intermediate Similarity	NPC11551
0.7679	Intermediate Similarity	NPC472949
0.7679	Intermediate Similarity	NPC309780
0.7679	Intermediate Similarity	NPC77689
0.7679	Intermediate Similarity	NPC473884
0.7679	Intermediate Similarity	NPC214484
0.7679	Intermediate Similarity	NPC157868
0.7679	Intermediate Similarity	NPC319570
0.7679	Intermediate Similarity	NPC180550
0.7679	Intermediate Similarity	NPC208381
0.7679	Intermediate Similarity	NPC114441
0.7679	Intermediate Similarity	NPC469945
0.7679	Intermediate Similarity	NPC6377
0.7677	Intermediate Similarity	NPC477436
0.7677	Intermediate Similarity	NPC477435
0.7672	Intermediate Similarity	NPC470882
0.7672	Intermediate Similarity	NPC473265
0.7672	Intermediate Similarity	NPC473253
0.767	Intermediate Similarity	NPC233012
0.767	Intermediate Similarity	NPC477871
0.767	Intermediate Similarity	NPC476213
0.767	Intermediate Similarity	NPC54909
0.767	Intermediate Similarity	NPC477870
0.767	Intermediate Similarity	NPC476246
0.7664	Intermediate Similarity	NPC173905
0.7664	Intermediate Similarity	NPC5475
0.7664	Intermediate Similarity	NPC42662
0.7664	Intermediate Similarity	NPC474242
0.7664	Intermediate Similarity	NPC41405
0.7664	Intermediate Similarity	NPC284828
0.7664	Intermediate Similarity	NPC472216
0.7664	Intermediate Similarity	NPC475922
0.7664	Intermediate Similarity	NPC250018

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 NPC469528 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1553
0.2-0.3	3698
0.3-0.4	2328
0.4-0.5	805
0.5-0.6	316
0.6-0.7	186
0.7-0.8	78
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
0.7938	Intermediate Similarity	NPD6411	Approved
0.7905	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD6319	Approved
0.7732	Intermediate Similarity	NPD6101	Approved
0.7732	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6083	Phase 2
0.7549	Intermediate Similarity	NPD6084	Phase 2
0.7545	Intermediate Similarity	NPD4632	Approved
0.7525	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5697	Approved
0.7455	Intermediate Similarity	NPD8297	Approved
0.7414	Intermediate Similarity	NPD8328	Phase 3
0.7407	Intermediate Similarity	NPD6899	Approved
0.7407	Intermediate Similarity	NPD6881	Approved
0.7383	Intermediate Similarity	NPD7128	Approved
0.7383	Intermediate Similarity	NPD6675	Approved
0.7383	Intermediate Similarity	NPD6402	Approved
0.7383	Intermediate Similarity	NPD5739	Approved
0.735	Intermediate Similarity	NPD7492	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.7327	Intermediate Similarity	NPD5779	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7327	Intermediate Similarity	NPD5778	Approved
0.7315	Intermediate Similarity	NPD6412	Phase 2
0.7315	Intermediate Similarity	NPD5701	Approved
0.7308	Intermediate Similarity	NPD5696	Approved
0.7304	Intermediate Similarity	NPD6054	Approved
0.7288	Intermediate Similarity	NPD6616	Approved
0.7273	Intermediate Similarity	NPD7102	Approved
0.7273	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD6883	Approved
0.7255	Intermediate Similarity	NPD5282	Discontinued
0.7248	Intermediate Similarity	NPD7320	Approved
0.7248	Intermediate Similarity	NPD6686	Approved
0.7248	Intermediate Similarity	NPD6011	Approved
0.7241	Intermediate Similarity	NPD6016	Approved
0.7241	Intermediate Similarity	NPD6015	Approved
0.7228	Intermediate Similarity	NPD7983	Approved
0.7227	Intermediate Similarity	NPD7078	Approved
0.7207	Intermediate Similarity	NPD8130	Phase 1
0.7207	Intermediate Similarity	NPD6649	Approved
0.7207	Intermediate Similarity	NPD6847	Approved
0.7207	Intermediate Similarity	NPD6617	Approved
0.7207	Intermediate Similarity	NPD6869	Approved
0.7207	Intermediate Similarity	NPD6650	Approved
0.72	Intermediate Similarity	NPD4753	Phase 2
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7193	Intermediate Similarity	NPD6009	Approved
0.7182	Intermediate Similarity	NPD6372	Approved
0.7182	Intermediate Similarity	NPD6373	Approved
0.7179	Intermediate Similarity	NPD6370	Approved
0.7179	Intermediate Similarity	NPD5988	Approved
0.7167	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.7094	Intermediate Similarity	NPD6921	Approved
0.7094	Intermediate Similarity	NPD5983	Phase 2
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7048	Intermediate Similarity	NPD4755	Approved
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5210	Approved
0.7019	Intermediate Similarity	NPD4629	Approved
0.701	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD3573	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6979	Remote Similarity	NPD4695	Discontinued
0.6975	Remote Similarity	NPD7604	Phase 2
0.6961	Remote Similarity	NPD6698	Approved
0.6961	Remote Similarity	NPD46	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD7748	Approved
0.6916	Remote Similarity	NPD4700	Approved
0.6903	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6098	Approved
0.6893	Remote Similarity	NPD5284	Approved
0.6893	Remote Similarity	NPD7515	Phase 2
0.6893	Remote Similarity	NPD5281	Approved
0.6893	Remote Similarity	NPD5694	Approved
0.6887	Remote Similarity	NPD7902	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6869	Remote Similarity	NPD4786	Approved
0.6863	Remote Similarity	NPD6673	Approved
0.6863	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6904	Approved
0.6863	Remote Similarity	NPD6080	Approved
0.686	Remote Similarity	NPD6336	Discontinued
0.6852	Remote Similarity	NPD5223	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.681	Remote Similarity	NPD6274	Approved
0.6807	Remote Similarity	NPD8513	Phase 3
0.6807	Remote Similarity	NPD8515	Approved
0.6807	Remote Similarity	NPD8517	Approved
0.6807	Remote Similarity	NPD8516	Approved
0.6796	Remote Similarity	NPD5692	Phase 3
0.6792	Remote Similarity	NPD5221	Approved
0.6792	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5222	Approved
0.678	Remote Similarity	NPD7101	Approved
0.678	Remote Similarity	NPD7100	Approved
0.6757	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.6735	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD6409	Approved
0.6733	Remote Similarity	NPD5330	Approved
0.6733	Remote Similarity	NPD7521	Approved
0.6733	Remote Similarity	NPD6684	Approved
0.6733	Remote Similarity	NPD5690	Phase 2
0.6733	Remote Similarity	NPD7334	Approved
0.6733	Remote Similarity	NPD5279	Phase 3
0.6733	Remote Similarity	NPD7146	Approved
0.6731	Remote Similarity	NPD6050	Approved
0.6731	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD5693	Phase 1
0.6729	Remote Similarity	NPD5173	Approved
0.6721	Remote Similarity	NPD7507	Approved
0.67	Remote Similarity	NPD3666	Approved
0.67	Remote Similarity	NPD4197	Approved
0.67	Remote Similarity	NPD3665	Phase 1
0.67	Remote Similarity	NPD3133	Approved
0.6698	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6053	Discontinued
0.6696	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6335	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.664	Remote Similarity	NPD5956	Approved
0.6639	Remote Similarity	NPD4522	Approved
0.6638	Remote Similarity	NPD8133	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6636	Remote Similarity	NPD4697	Phase 3
0.6634	Remote Similarity	NPD5329	Approved
0.6613	Remote Similarity	NPD6033	Approved
0.6607	Remote Similarity	NPD4768	Approved
0.6607	Remote Similarity	NPD4767	Approved
0.6606	Remote Similarity	NPD7640	Approved
0.6606	Remote Similarity	NPD7639	Approved
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7900	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6602	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4754	Approved
0.6571	Remote Similarity	NPD6079	Approved
0.6569	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3618	Phase 1
0.6569	Remote Similarity	NPD5280	Approved
0.6569	Remote Similarity	NPD4694	Approved
0.6538	Remote Similarity	NPD5328	Approved
0.6535	Remote Similarity	NPD3668	Phase 3
0.6532	Remote Similarity	NPD8074	Phase 3
0.6529	Remote Similarity	NPD6909	Approved
0.6529	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6908	Approved
0.6525	Remote Similarity	NPD6868	Approved
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5248	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.6522	Remote Similarity	NPD5250	Approved
0.6509	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD4221	Approved
0.65	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4223	Phase 3
0.6491	Remote Similarity	NPD5128	Approved
0.6481	Remote Similarity	NPD7839	Suspended
0.6476	Remote Similarity	NPD5207	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6465	Remote Similarity	NPD5368	Approved
0.6458	Remote Similarity	NPD3702	Approved
0.6457	Remote Similarity	NPD7260	Phase 2
0.6442	Remote Similarity	NPD5208	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6415	Remote Similarity	NPD8035	Phase 2
0.6415	Remote Similarity	NPD8034	Phase 2
0.6408	Remote Similarity	NPD5786	Approved
0.6408	Remote Similarity	NPD4623	Approved
0.6408	Remote Similarity	NPD4519	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data