NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	251.764
LogP:	4.166
LogD:	4.039
LogS:	-4.437
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	4.032
Fsp3:	0.667
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:	-4.611
MDCK Permeability:	2.251321348012425e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.193
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.56
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226
Plasma Protein Binding (PPB):	94.1011962890625%
Volume Distribution (VD):	2.745
Pgp-substrate:	3.2861411571502686%

ADMET: Metabolism

CYP1A2-inhibitor:	0.534
CYP1A2-substrate:	0.185
CYP2C19-inhibitor:	0.766
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.494
CYP2C9-substrate:	0.146
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.221
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	12.603
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.766
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.831
Skin Sensitization:	0.908
Carcinogencity:	0.562
Eye Corrosion:	0.91
Eye Irritation:	0.863
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC276764

Natural Product ID:	NPC276764
*Common Name:**	Xenitorin B
IUPAC Name:	(1R,4aR,7S,8aR)-4,7-dimethyl-1-prop-1-en-2-yl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one
Synonyms:
Standard InCHIKey:	SIZHTHJIDBXZNM-DNVSUFBTSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-9(2)15-13-7-10(3)5-6-12(13)11(4)8-14(15)16/h8,10,12-13,15H,1,5-7H2,2-4H3/t10-,12-,13+,15-/m0/s1
SMILES:	C[C@H]1CC[C@@H]2[C@@H](C1)[C@H](C(=C)C)C(=O)C=C2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449506
PubChem CID:	11830928
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32497	xenia puerto-galerae	Species	n.a.	n.a.	n.a.	Formosan soft coral	n.a.	PMID[12502327]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[550682]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[550682]

☑ 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 NPC276764 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	224
0.1-0.2	2223
0.2-0.3	12691
0.3-0.4	14995
0.4-0.5	7524
0.5-0.6	3781
0.6-0.7	1001
0.7-0.8	219
0.8-0.85	28
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472304
0.9474	High Similarity	NPC127582
0.9322	High Similarity	NPC475124
0.9322	High Similarity	NPC285371
0.9123	High Similarity	NPC56905
0.9123	High Similarity	NPC27610
0.8909	High Similarity	NPC268564
0.873	High Similarity	NPC260474
0.873	High Similarity	NPC188292
0.873	High Similarity	NPC310992
0.8689	High Similarity	NPC469662
0.8689	High Similarity	NPC6697
0.8667	High Similarity	NPC213152
0.8621	High Similarity	NPC115385
0.8594	High Similarity	NPC139397
0.8548	High Similarity	NPC251118
0.8525	High Similarity	NPC202118
0.8525	High Similarity	NPC197238
0.8525	High Similarity	NPC288253
0.8475	Intermediate Similarity	NPC308108
0.8475	Intermediate Similarity	NPC170799
0.8462	Intermediate Similarity	NPC265782
0.8462	Intermediate Similarity	NPC307176
0.8462	Intermediate Similarity	NPC2634
0.8462	Intermediate Similarity	NPC251929
0.8462	Intermediate Similarity	NPC35734
0.8462	Intermediate Similarity	NPC282593
0.8462	Intermediate Similarity	NPC260040
0.8462	Intermediate Similarity	NPC159577
0.8438	Intermediate Similarity	NPC87141
0.8438	Intermediate Similarity	NPC155198
0.8387	Intermediate Similarity	NPC212210
0.8364	Intermediate Similarity	NPC32351
0.8361	Intermediate Similarity	NPC60565
0.8333	Intermediate Similarity	NPC190035
0.8333	Intermediate Similarity	NPC54123
0.8333	Intermediate Similarity	NPC474562
0.8333	Intermediate Similarity	NPC115023
0.8308	Intermediate Similarity	NPC256846
0.8281	Intermediate Similarity	NPC4370
0.8281	Intermediate Similarity	NPC290350
0.8276	Intermediate Similarity	NPC200258
0.8226	Intermediate Similarity	NPC165695
0.8209	Intermediate Similarity	NPC56747
0.8209	Intermediate Similarity	NPC470044
0.8209	Intermediate Similarity	NPC180015
0.8209	Intermediate Similarity	NPC303613
0.8209	Intermediate Similarity	NPC130016
0.8209	Intermediate Similarity	NPC109576
0.8209	Intermediate Similarity	NPC470045
0.8209	Intermediate Similarity	NPC251705
0.8209	Intermediate Similarity	NPC474228
0.8167	Intermediate Similarity	NPC311852
0.8154	Intermediate Similarity	NPC82477
0.8154	Intermediate Similarity	NPC142754
0.8154	Intermediate Similarity	NPC39157
0.8154	Intermediate Similarity	NPC20610
0.8154	Intermediate Similarity	NPC296697
0.8136	Intermediate Similarity	NPC473733
0.8125	Intermediate Similarity	NPC323005
0.806	Intermediate Similarity	NPC234707
0.806	Intermediate Similarity	NPC225467
0.8036	Intermediate Similarity	NPC176819
0.8036	Intermediate Similarity	NPC58970
0.8036	Intermediate Similarity	NPC163984
0.803	Intermediate Similarity	NPC286814
0.803	Intermediate Similarity	NPC182815
0.8	Intermediate Similarity	NPC193695
0.8	Intermediate Similarity	NPC91962
0.8	Intermediate Similarity	NPC220210
0.8	Intermediate Similarity	NPC475523
0.8	Intermediate Similarity	NPC20181
0.8	Intermediate Similarity	NPC192427
0.7971	Intermediate Similarity	NPC65650
0.7971	Intermediate Similarity	NPC476346
0.7971	Intermediate Similarity	NPC293803
0.7971	Intermediate Similarity	NPC473171
0.7969	Intermediate Similarity	NPC470329
0.7966	Intermediate Similarity	NPC275472
0.7937	Intermediate Similarity	NPC472306
0.7931	Intermediate Similarity	NPC23117
0.7931	Intermediate Similarity	NPC474141
0.7895	Intermediate Similarity	NPC236623
0.7895	Intermediate Similarity	NPC64866
0.7895	Intermediate Similarity	NPC27438
0.7869	Intermediate Similarity	NPC60772
0.7869	Intermediate Similarity	NPC94991
0.7869	Intermediate Similarity	NPC266295
0.7857	Intermediate Similarity	NPC1254
0.7857	Intermediate Similarity	NPC76966
0.7857	Intermediate Similarity	NPC186554
0.7857	Intermediate Similarity	NPC180886
0.7857	Intermediate Similarity	NPC151622
0.7857	Intermediate Similarity	NPC472305
0.7857	Intermediate Similarity	NPC69408
0.7857	Intermediate Similarity	NPC7629
0.7833	Intermediate Similarity	NPC20603
0.7826	Intermediate Similarity	NPC474796
0.7826	Intermediate Similarity	NPC474797
0.7826	Intermediate Similarity	NPC329866
0.7826	Intermediate Similarity	NPC255021
0.7826	Intermediate Similarity	NPC309852
0.7818	Intermediate Similarity	NPC14917
0.7818	Intermediate Similarity	NPC4079
0.7818	Intermediate Similarity	NPC236355
0.7797	Intermediate Similarity	NPC202850
0.7797	Intermediate Similarity	NPC63396
0.7797	Intermediate Similarity	NPC5626
0.7794	Intermediate Similarity	NPC470078
0.7794	Intermediate Similarity	NPC21944
0.7794	Intermediate Similarity	NPC5701
0.7794	Intermediate Similarity	NPC133253
0.7794	Intermediate Similarity	NPC305501
0.7746	Intermediate Similarity	NPC266193
0.7746	Intermediate Similarity	NPC34110
0.7746	Intermediate Similarity	NPC257666
0.7746	Intermediate Similarity	NPC472300
0.7742	Intermediate Similarity	NPC285594
0.7742	Intermediate Similarity	NPC259261
0.7742	Intermediate Similarity	NPC96551
0.7742	Intermediate Similarity	NPC143834
0.7727	Intermediate Similarity	NPC193770
0.7719	Intermediate Similarity	NPC116906
0.7681	Intermediate Similarity	NPC474488
0.7656	Intermediate Similarity	NPC32285
0.7647	Intermediate Similarity	NPC246722
0.7647	Intermediate Similarity	NPC477856
0.7647	Intermediate Similarity	NPC214770
0.7647	Intermediate Similarity	NPC151045
0.7639	Intermediate Similarity	NPC275494
0.7639	Intermediate Similarity	NPC115515
0.7639	Intermediate Similarity	NPC189485
0.7639	Intermediate Similarity	NPC207772
0.7639	Intermediate Similarity	NPC471409
0.7627	Intermediate Similarity	NPC14002
0.7619	Intermediate Similarity	NPC25853
0.7606	Intermediate Similarity	NPC469793
0.7606	Intermediate Similarity	NPC469796
0.7606	Intermediate Similarity	NPC263582
0.7581	Intermediate Similarity	NPC30215
0.7576	Intermediate Similarity	NPC176171
0.7576	Intermediate Similarity	NPC92327
0.7571	Intermediate Similarity	NPC211641
0.7571	Intermediate Similarity	NPC20025
0.7571	Intermediate Similarity	NPC128346
0.7571	Intermediate Similarity	NPC219232
0.7538	Intermediate Similarity	NPC4638
0.7538	Intermediate Similarity	NPC150162
0.7536	Intermediate Similarity	NPC181204
0.7536	Intermediate Similarity	NPC223187
0.7534	Intermediate Similarity	NPC90965
0.7534	Intermediate Similarity	NPC27817
0.7534	Intermediate Similarity	NPC170793
0.75	Intermediate Similarity	NPC209431
0.75	Intermediate Similarity	NPC165711
0.75	Intermediate Similarity	NPC97377
0.75	Intermediate Similarity	NPC474060
0.75	Intermediate Similarity	NPC197659
0.75	Intermediate Similarity	NPC100809
0.7465	Intermediate Similarity	NPC255650
0.7463	Intermediate Similarity	NPC176107
0.7455	Intermediate Similarity	NPC25771
0.7432	Intermediate Similarity	NPC474509
0.7432	Intermediate Similarity	NPC250632
0.7432	Intermediate Similarity	NPC476809
0.7432	Intermediate Similarity	NPC108955
0.7432	Intermediate Similarity	NPC2482
0.7429	Intermediate Similarity	NPC35656
0.7424	Intermediate Similarity	NPC268039
0.7419	Intermediate Similarity	NPC267626
0.7419	Intermediate Similarity	NPC49575
0.7419	Intermediate Similarity	NPC55004
0.7419	Intermediate Similarity	NPC230823
0.7397	Intermediate Similarity	NPC74410
0.7397	Intermediate Similarity	NPC253561
0.7397	Intermediate Similarity	NPC62336
0.7397	Intermediate Similarity	NPC80088
0.7397	Intermediate Similarity	NPC469996
0.7391	Intermediate Similarity	NPC40574
0.7361	Intermediate Similarity	NPC19907
0.7361	Intermediate Similarity	NPC470525
0.7344	Intermediate Similarity	NPC270042
0.7333	Intermediate Similarity	NPC99308
0.7333	Intermediate Similarity	NPC45283
0.7333	Intermediate Similarity	NPC474085
0.7333	Intermediate Similarity	NPC477372
0.7333	Intermediate Similarity	NPC278459
0.7333	Intermediate Similarity	NPC44963
0.7333	Intermediate Similarity	NPC226068
0.7333	Intermediate Similarity	NPC475833
0.7333	Intermediate Similarity	NPC121984
0.7333	Intermediate Similarity	NPC189237
0.7333	Intermediate Similarity	NPC116797
0.7333	Intermediate Similarity	NPC471898
0.7333	Intermediate Similarity	NPC149237
0.7333	Intermediate Similarity	NPC472684
0.7333	Intermediate Similarity	NPC55869
0.7297	Intermediate Similarity	NPC308038
0.7297	Intermediate Similarity	NPC476177
0.7286	Intermediate Similarity	NPC84790

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 NPC276764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	2433
0.2-0.3	4318
0.3-0.4	1566
0.4-0.5	368
0.5-0.6	168
0.6-0.7	66
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8594	High Similarity	NPD4137	Phase 3
0.8475	Intermediate Similarity	NPD287	Approved
0.8462	Intermediate Similarity	NPD4691	Approved
0.8462	Intermediate Similarity	NPD4747	Approved
0.8154	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD4058	Approved
0.8088	Intermediate Similarity	NPD5733	Approved
0.8088	Intermediate Similarity	NPD4687	Approved
0.806	Intermediate Similarity	NPD5276	Approved
0.7237	Intermediate Similarity	NPD4221	Approved
0.7237	Intermediate Similarity	NPD4223	Phase 3
0.72	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8028	Phase 2
0.7059	Intermediate Similarity	NPD7331	Phase 2
0.7051	Intermediate Similarity	NPD3133	Approved
0.7051	Intermediate Similarity	NPD3665	Phase 1
0.7051	Intermediate Similarity	NPD4197	Approved
0.7051	Intermediate Similarity	NPD3666	Approved
0.6962	Remote Similarity	NPD5329	Approved
0.6933	Remote Similarity	NPD3617	Approved
0.6875	Remote Similarity	NPD3618	Phase 1
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD4623	Approved
0.6875	Remote Similarity	NPD5280	Approved
0.6875	Remote Similarity	NPD4688	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD5205	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD4693	Phase 3
0.6875	Remote Similarity	NPD7521	Approved
0.6875	Remote Similarity	NPD4138	Approved
0.6875	Remote Similarity	NPD4689	Approved
0.6875	Remote Similarity	NPD4694	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD4519	Discontinued
0.6875	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD7334	Approved
0.6795	Remote Similarity	NPD3667	Approved
0.679	Remote Similarity	NPD3573	Approved
0.6707	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6903	Approved
0.6707	Remote Similarity	NPD5737	Approved
0.6707	Remote Similarity	NPD5208	Approved
0.6707	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7341	Phase 2
0.6627	Remote Similarity	NPD5328	Approved
0.6627	Remote Similarity	NPD6904	Approved
0.6627	Remote Similarity	NPD6673	Approved
0.6627	Remote Similarity	NPD4753	Phase 2
0.6627	Remote Similarity	NPD6080	Approved
0.6625	Remote Similarity	NPD4786	Approved
0.6625	Remote Similarity	NPD3668	Phase 3
0.6548	Remote Similarity	NPD5207	Approved
0.6548	Remote Similarity	NPD5692	Phase 3
0.6471	Remote Similarity	NPD5693	Phase 1
0.6471	Remote Similarity	NPD5281	Approved
0.6471	Remote Similarity	NPD6050	Approved
0.6471	Remote Similarity	NPD7515	Phase 2
0.6471	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD5694	Approved
0.6471	Remote Similarity	NPD5284	Approved
0.6463	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4195	Approved
0.6395	Remote Similarity	NPD4202	Approved
0.6395	Remote Similarity	NPD7631	Approved
0.6375	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4096	Approved
0.6341	Remote Similarity	NPD1694	Approved
0.6322	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6001	Approved
0.6322	Remote Similarity	NPD7748	Approved
0.6322	Remote Similarity	NPD7900	Approved
0.6308	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7609	Phase 3
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD4692	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4629	Approved
0.625	Remote Similarity	NPD4139	Approved
0.6207	Remote Similarity	NPD5133	Approved
0.6207	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.619	Remote Similarity	NPD650	Approved
0.6182	Remote Similarity	NPD319	Phase 1
0.618	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4697	Phase 3
0.618	Remote Similarity	NPD5221	Approved
0.618	Remote Similarity	NPD5222	Approved
0.6143	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4518	Approved
0.6111	Remote Similarity	NPD6083	Phase 2
0.6111	Remote Similarity	NPD3495	Discontinued
0.6111	Remote Similarity	NPD6084	Phase 2
0.6111	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5173	Approved
0.6111	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD4755	Approved
0.6067	Remote Similarity	NPD5654	Approved
0.6044	Remote Similarity	NPD5696	Approved
0.6023	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD7614	Phase 1
0.6	Remote Similarity	NPD7732	Phase 3
0.6	Remote Similarity	NPD4191	Approved
0.5978	Remote Similarity	NPD4700	Approved
0.5978	Remote Similarity	NPD4696	Approved
0.5978	Remote Similarity	NPD5286	Approved
0.5978	Remote Similarity	NPD5285	Approved
0.5965	Remote Similarity	NPD5783	Phase 3
0.5934	Remote Similarity	NPD5959	Approved
0.5921	Remote Similarity	NPD4243	Approved
0.5914	Remote Similarity	NPD5223	Approved
0.5904	Remote Similarity	NPD4788	Approved
0.5851	Remote Similarity	NPD5226	Approved
0.5851	Remote Similarity	NPD5211	Phase 2
0.5851	Remote Similarity	NPD5091	Approved
0.5851	Remote Similarity	NPD4633	Approved
0.5851	Remote Similarity	NPD5225	Approved
0.5851	Remote Similarity	NPD5224	Approved
0.5789	Remote Similarity	NPD5175	Approved
0.5789	Remote Similarity	NPD4754	Approved
0.5789	Remote Similarity	NPD6052	Approved
0.5789	Remote Similarity	NPD5174	Approved
0.5778	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4785	Approved
0.5769	Remote Similarity	NPD4784	Approved
0.5765	Remote Similarity	NPD1696	Phase 3
0.5732	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5141	Approved
0.5696	Remote Similarity	NPD5275	Approved
0.5696	Remote Similarity	NPD6942	Approved
0.5696	Remote Similarity	NPD7339	Approved
0.5696	Remote Similarity	NPD4190	Phase 3
0.5696	Remote Similarity	NPD8039	Approved
0.567	Remote Similarity	NPD7128	Approved
0.567	Remote Similarity	NPD4768	Approved
0.567	Remote Similarity	NPD4767	Approved
0.567	Remote Similarity	NPD6402	Approved
0.567	Remote Similarity	NPD6008	Approved
0.567	Remote Similarity	NPD5739	Approved
0.567	Remote Similarity	NPD6675	Approved
0.5663	Remote Similarity	NPD942	Approved
0.5638	Remote Similarity	NPD6404	Discontinued
0.5625	Remote Similarity	NPD8262	Approved
0.5625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5697	Approved
0.5612	Remote Similarity	NPD5701	Approved
0.5612	Remote Similarity	NPD6412	Phase 2
0.5612	Remote Similarity	NPD6614	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