NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	1.815
LogD:	1.691
LogS:	-2.95
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	4.327
Fsp3:	0.667
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:	-4.664
MDCK Permeability:	2.131986548192799e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.763
Plasma Protein Binding (PPB):	86.63166046142578%
Volume Distribution (VD):	0.919
Pgp-substrate:	16.26361656188965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.551
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.25
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	4.139
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.319
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.143
Skin Sensitization:	0.161
Carcinogencity:	0.405
Eye Corrosion:	0.006
Eye Irritation:	0.084
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC470298

Natural Product ID:	NPC470298
*Common Name:**	Oxyphyllanene F
IUPAC Name:	(4aR)-7-(1,2-dihydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6-tetrahydronaphthalen-2-one
Synonyms:	Oxyphyllanene F
Standard InCHIKey:	FPOORCYPPCUIJT-GICMACPYSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-10-12-8-11(15(3,18)9-16)4-6-14(12,2)7-5-13(10)17/h8,16,18H,4-7,9H2,1-3H3/t14-,15?/m1/s1
SMILES:	OCC(C1=CC2=C(C)C(=O)CC[C@]2(CC1)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1949799
PubChem CID:	57393408
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(81)85171-0]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11514174]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	fruit	Hainan Island, China	1998	PMID[12398545]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22277277]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23583435]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25757283]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	13.95	ug.mL-1	PMID[506141]
NPT34	Cell Line	BV-2	Mus musculus	MNTD	=	0.1	uM	PMID[506142]

☑ 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 NPC470298 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	174
0.1-0.2	1034
0.2-0.3	4843
0.3-0.4	12592
0.4-0.5	13723
0.5-0.6	7154
0.6-0.7	2741
0.7-0.8	400
0.8-0.85	29
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8554	High Similarity	NPC15807
0.8537	High Similarity	NPC251475
0.8537	High Similarity	NPC169941
0.85	High Similarity	NPC281138
0.8354	Intermediate Similarity	NPC263582
0.8354	Intermediate Similarity	NPC470525
0.8333	Intermediate Similarity	NPC470299
0.8312	Intermediate Similarity	NPC84790
0.8293	Intermediate Similarity	NPC121984
0.8272	Intermediate Similarity	NPC308038
0.8235	Intermediate Similarity	NPC472974
0.8228	Intermediate Similarity	NPC114236
0.8205	Intermediate Similarity	NPC247586
0.8182	Intermediate Similarity	NPC116726
0.8171	Intermediate Similarity	NPC172013
0.8148	Intermediate Similarity	NPC62336
0.8148	Intermediate Similarity	NPC475994
0.814	Intermediate Similarity	NPC287079
0.8132	Intermediate Similarity	NPC161147
0.8095	Intermediate Similarity	NPC66764
0.8095	Intermediate Similarity	NPC110150
0.8072	Intermediate Similarity	NPC6663
0.8068	Intermediate Similarity	NPC473099
0.8049	Intermediate Similarity	NPC19900
0.8025	Intermediate Similarity	NPC74995
0.8025	Intermediate Similarity	NPC266193
0.8025	Intermediate Similarity	NPC197659
0.8025	Intermediate Similarity	NPC257666
0.8	Intermediate Similarity	NPC40687
0.8	Intermediate Similarity	NPC196227
0.8	Intermediate Similarity	NPC476412
0.7976	Intermediate Similarity	NPC158411
0.7976	Intermediate Similarity	NPC93590
0.7976	Intermediate Similarity	NPC38796
0.7955	Intermediate Similarity	NPC36668
0.7955	Intermediate Similarity	NPC473100
0.7955	Intermediate Similarity	NPC118011
0.7952	Intermediate Similarity	NPC271104
0.7952	Intermediate Similarity	NPC2482
0.7935	Intermediate Similarity	NPC474785
0.7935	Intermediate Similarity	NPC135685
0.7935	Intermediate Similarity	NPC474938
0.7935	Intermediate Similarity	NPC470522
0.7927	Intermediate Similarity	NPC275494
0.7927	Intermediate Similarity	NPC471409
0.7927	Intermediate Similarity	NPC178852
0.7907	Intermediate Similarity	NPC179006
0.7907	Intermediate Similarity	NPC474853
0.7907	Intermediate Similarity	NPC187529
0.7901	Intermediate Similarity	NPC472305
0.7895	Intermediate Similarity	NPC473624
0.7889	Intermediate Similarity	NPC109305
0.7889	Intermediate Similarity	NPC474736
0.7875	Intermediate Similarity	NPC215050
0.7865	Intermediate Similarity	NPC69622
0.7841	Intermediate Similarity	NPC72397
0.7831	Intermediate Similarity	NPC152061
0.7826	Intermediate Similarity	NPC117133
0.7821	Intermediate Similarity	NPC473893
0.7816	Intermediate Similarity	NPC473168
0.7816	Intermediate Similarity	NPC89077
0.7816	Intermediate Similarity	NPC194417
0.7805	Intermediate Similarity	NPC34110
0.7805	Intermediate Similarity	NPC325946
0.7805	Intermediate Similarity	NPC86917
0.7802	Intermediate Similarity	NPC474882
0.7802	Intermediate Similarity	NPC472977
0.7802	Intermediate Similarity	NPC472976
0.7802	Intermediate Similarity	NPC473162
0.7778	Intermediate Similarity	NPC19114
0.7778	Intermediate Similarity	NPC475441
0.775	Intermediate Similarity	NPC186042
0.7738	Intermediate Similarity	NPC148685
0.7738	Intermediate Similarity	NPC472301
0.7738	Intermediate Similarity	NPC157895
0.7738	Intermediate Similarity	NPC104120
0.7738	Intermediate Similarity	NPC45495
0.7727	Intermediate Similarity	NPC136548
0.7711	Intermediate Similarity	NPC297996
0.7711	Intermediate Similarity	NPC189485
0.7701	Intermediate Similarity	NPC476426
0.7701	Intermediate Similarity	NPC474083
0.7692	Intermediate Similarity	NPC472942
0.7683	Intermediate Similarity	NPC250621
0.7683	Intermediate Similarity	NPC151622
0.7683	Intermediate Similarity	NPC7629
0.7674	Intermediate Similarity	NPC49019
0.7674	Intermediate Similarity	NPC64600
0.7667	Intermediate Similarity	NPC134321
0.7667	Intermediate Similarity	NPC48010
0.766	Intermediate Similarity	NPC166745
0.766	Intermediate Similarity	NPC235464
0.766	Intermediate Similarity	NPC471717
0.7654	Intermediate Similarity	NPC213223
0.7647	Intermediate Similarity	NPC226068
0.7647	Intermediate Similarity	NPC116797
0.7647	Intermediate Similarity	NPC225515
0.764	Intermediate Similarity	NPC44181
0.7619	Intermediate Similarity	NPC474113
0.7619	Intermediate Similarity	NPC7232
0.7614	Intermediate Similarity	NPC179591
0.7614	Intermediate Similarity	NPC239685
0.7614	Intermediate Similarity	NPC470955
0.7614	Intermediate Similarity	NPC472985
0.7614	Intermediate Similarity	NPC472986
0.7609	Intermediate Similarity	NPC474690
0.7609	Intermediate Similarity	NPC299100
0.7609	Intermediate Similarity	NPC473172
0.7604	Intermediate Similarity	NPC473424
0.759	Intermediate Similarity	NPC203403
0.759	Intermediate Similarity	NPC97377
0.759	Intermediate Similarity	NPC471061
0.7586	Intermediate Similarity	NPC472326
0.7586	Intermediate Similarity	NPC473246
0.7582	Intermediate Similarity	NPC475806
0.7564	Intermediate Similarity	NPC278895
0.7558	Intermediate Similarity	NPC212083
0.7558	Intermediate Similarity	NPC103486
0.7556	Intermediate Similarity	NPC472973
0.7556	Intermediate Similarity	NPC472688
0.7556	Intermediate Similarity	NPC309603
0.7556	Intermediate Similarity	NPC472983
0.7556	Intermediate Similarity	NPC214387
0.7556	Intermediate Similarity	NPC472676
0.7556	Intermediate Similarity	NPC123912
0.7556	Intermediate Similarity	NPC473999
0.7556	Intermediate Similarity	NPC474918
0.7553	Intermediate Similarity	NPC208094
0.7531	Intermediate Similarity	NPC29542
0.7531	Intermediate Similarity	NPC201562
0.7531	Intermediate Similarity	NPC323437
0.7529	Intermediate Similarity	NPC74086
0.7529	Intermediate Similarity	NPC306095
0.7529	Intermediate Similarity	NPC470946
0.7529	Intermediate Similarity	NPC470945
0.7529	Intermediate Similarity	NPC108955
0.7529	Intermediate Similarity	NPC471514
0.7529	Intermediate Similarity	NPC470947
0.7528	Intermediate Similarity	NPC470523
0.7528	Intermediate Similarity	NPC220930
0.7528	Intermediate Similarity	NPC272039
0.7528	Intermediate Similarity	NPC181327
0.7528	Intermediate Similarity	NPC312561
0.7527	Intermediate Similarity	NPC180950
0.7527	Intermediate Similarity	NPC472932
0.7527	Intermediate Similarity	NPC259286
0.7526	Intermediate Similarity	NPC475050
0.75	Intermediate Similarity	NPC134826
0.75	Intermediate Similarity	NPC231739
0.75	Intermediate Similarity	NPC250575
0.75	Intermediate Similarity	NPC74410
0.75	Intermediate Similarity	NPC32037
0.75	Intermediate Similarity	NPC472930
0.75	Intermediate Similarity	NPC70685
0.75	Intermediate Similarity	NPC478122
0.75	Intermediate Similarity	NPC471224
0.75	Intermediate Similarity	NPC274724
0.75	Intermediate Similarity	NPC169095
0.75	Intermediate Similarity	NPC173321
0.75	Intermediate Similarity	NPC469948
0.75	Intermediate Similarity	NPC79573
0.75	Intermediate Similarity	NPC69454
0.7473	Intermediate Similarity	NPC129913
0.7473	Intermediate Similarity	NPC477149
0.7473	Intermediate Similarity	NPC128672
0.7473	Intermediate Similarity	NPC477147
0.7471	Intermediate Similarity	NPC105173
0.7471	Intermediate Similarity	NPC477785
0.7471	Intermediate Similarity	NPC477784
0.7471	Intermediate Similarity	NPC477786
0.7471	Intermediate Similarity	NPC297398
0.7447	Intermediate Similarity	NPC471463
0.7447	Intermediate Similarity	NPC473164
0.7447	Intermediate Similarity	NPC249954
0.7444	Intermediate Similarity	NPC470524
0.7444	Intermediate Similarity	NPC471793
0.7444	Intermediate Similarity	NPC471722
0.7444	Intermediate Similarity	NPC53454
0.7444	Intermediate Similarity	NPC471791
0.7444	Intermediate Similarity	NPC474854
0.7442	Intermediate Similarity	NPC275766
0.7442	Intermediate Similarity	NPC136150
0.7442	Intermediate Similarity	NPC4166
0.7442	Intermediate Similarity	NPC55869
0.7439	Intermediate Similarity	NPC301065
0.7419	Intermediate Similarity	NPC181393
0.7419	Intermediate Similarity	NPC8993
0.7419	Intermediate Similarity	NPC78159
0.7419	Intermediate Similarity	NPC217624
0.7416	Intermediate Similarity	NPC474733
0.7416	Intermediate Similarity	NPC82979
0.7416	Intermediate Similarity	NPC475022
0.7416	Intermediate Similarity	NPC474778
0.7416	Intermediate Similarity	NPC145879
0.7416	Intermediate Similarity	NPC474732
0.7416	Intermediate Similarity	NPC118648
0.7416	Intermediate Similarity	NPC94666
0.7416	Intermediate Similarity	NPC473226
0.7416	Intermediate Similarity	NPC31564
0.7416	Intermediate Similarity	NPC222613

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 NPC470298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1502
0.2-0.3	3774
0.3-0.4	2500
0.4-0.5	804
0.5-0.6	310
0.6-0.7	84
0.7-0.8	8
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
0.7701	Intermediate Similarity	NPD1696	Phase 3
0.7614	Intermediate Similarity	NPD5279	Phase 3
0.7529	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4519	Discontinued
0.7416	Intermediate Similarity	NPD4623	Approved
0.7416	Intermediate Similarity	NPD5280	Approved
0.7416	Intermediate Similarity	NPD4694	Approved
0.7386	Intermediate Similarity	NPD3133	Approved
0.7386	Intermediate Similarity	NPD3666	Approved
0.7386	Intermediate Similarity	NPD3665	Phase 1
0.7356	Intermediate Similarity	NPD3667	Approved
0.7253	Intermediate Similarity	NPD4518	Approved
0.7222	Intermediate Similarity	NPD3618	Phase 1
0.7215	Intermediate Similarity	NPD7331	Phase 2
0.7191	Intermediate Similarity	NPD4786	Approved
0.7174	Intermediate Similarity	NPD4753	Phase 2
0.7159	Intermediate Similarity	NPD4221	Approved
0.7159	Intermediate Similarity	NPD4223	Phase 3
0.7126	Intermediate Similarity	NPD4695	Discontinued
0.7033	Intermediate Similarity	NPD5690	Phase 2
0.7021	Intermediate Similarity	NPD5281	Approved
0.7021	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD4197	Approved
0.6989	Remote Similarity	NPD5328	Approved
0.6989	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4202	Approved
0.6947	Remote Similarity	NPD5779	Approved
0.6947	Remote Similarity	NPD5778	Approved
0.6941	Remote Similarity	NPD8264	Approved
0.6923	Remote Similarity	NPD5329	Approved
0.6915	Remote Similarity	NPD4096	Approved
0.6875	Remote Similarity	NPD7341	Phase 2
0.686	Remote Similarity	NPD6933	Approved
0.6848	Remote Similarity	NPD5205	Approved
0.6848	Remote Similarity	NPD4689	Approved
0.6848	Remote Similarity	NPD4690	Approved
0.6848	Remote Similarity	NPD4138	Approved
0.6848	Remote Similarity	NPD4688	Approved
0.6848	Remote Similarity	NPD4693	Phase 3
0.6842	Remote Similarity	NPD6411	Approved
0.6842	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD7515	Phase 2
0.6804	Remote Similarity	NPD5695	Phase 3
0.6804	Remote Similarity	NPD5210	Approved
0.6804	Remote Similarity	NPD4629	Approved
0.6782	Remote Similarity	NPD4756	Discovery
0.6771	Remote Similarity	NPD5133	Approved
0.6744	Remote Similarity	NPD8039	Approved
0.6733	Remote Similarity	NPD5211	Phase 2
0.6705	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6101	Approved
0.663	Remote Similarity	NPD3668	Phase 3
0.6628	Remote Similarity	NPD4687	Approved
0.6628	Remote Similarity	NPD6924	Approved
0.6628	Remote Similarity	NPD6926	Approved
0.6628	Remote Similarity	NPD5733	Approved
0.6602	Remote Similarity	NPD5141	Approved
0.6588	Remote Similarity	NPD5276	Approved
0.6579	Remote Similarity	NPD342	Phase 1
0.6566	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4697	Phase 3
0.6566	Remote Similarity	NPD5221	Approved
0.6562	Remote Similarity	NPD5207	Approved
0.6562	Remote Similarity	NPD5692	Phase 3
0.6559	Remote Similarity	NPD1694	Approved
0.6556	Remote Similarity	NPD6931	Approved
0.6556	Remote Similarity	NPD6930	Phase 2
0.6545	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD5286	Approved
0.6535	Remote Similarity	NPD6404	Discontinued
0.6535	Remote Similarity	NPD4696	Approved
0.6535	Remote Similarity	NPD5285	Approved
0.6535	Remote Similarity	NPD4700	Approved
0.6531	Remote Similarity	NPD7748	Approved
0.6522	Remote Similarity	NPD4788	Approved
0.6517	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4194	Approved
0.65	Remote Similarity	NPD4192	Approved
0.65	Remote Similarity	NPD4193	Approved
0.65	Remote Similarity	NPD368	Approved
0.65	Remote Similarity	NPD4191	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6495	Remote Similarity	NPD6050	Approved
0.6495	Remote Similarity	NPD5694	Approved
0.6494	Remote Similarity	NPD4219	Approved
0.6489	Remote Similarity	NPD7521	Approved
0.6489	Remote Similarity	NPD7334	Approved
0.6489	Remote Similarity	NPD5330	Approved
0.6489	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD7146	Approved
0.6489	Remote Similarity	NPD6684	Approved
0.6484	Remote Similarity	NPD4139	Approved
0.6484	Remote Similarity	NPD4692	Approved
0.6471	Remote Similarity	NPD5223	Approved
0.6444	Remote Similarity	NPD4195	Approved
0.6444	Remote Similarity	NPD6929	Approved
0.6437	Remote Similarity	NPD4058	Approved
0.6436	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD6399	Phase 3
0.6421	Remote Similarity	NPD7524	Approved
0.642	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5224	Approved
0.6408	Remote Similarity	NPD4633	Approved
0.6408	Remote Similarity	NPD5225	Approved
0.6408	Remote Similarity	NPD5226	Approved
0.6392	Remote Similarity	NPD5785	Approved
0.6392	Remote Similarity	NPD46	Approved
0.6392	Remote Similarity	NPD6698	Approved
0.6386	Remote Similarity	NPD3704	Approved
0.6383	Remote Similarity	NPD5363	Approved
0.6374	Remote Similarity	NPD7332	Phase 2
0.6374	Remote Similarity	NPD7514	Phase 3
0.6354	Remote Similarity	NPD5737	Approved
0.6354	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD6903	Approved
0.6354	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4137	Phase 3
0.6346	Remote Similarity	NPD5175	Approved
0.6346	Remote Similarity	NPD5174	Approved
0.6346	Remote Similarity	NPD4754	Approved
0.6344	Remote Similarity	NPD6695	Phase 3
0.6337	Remote Similarity	NPD7902	Approved
0.6327	Remote Similarity	NPD7983	Approved
0.6321	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD4634	Approved
0.6292	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4691	Approved
0.6279	Remote Similarity	NPD4747	Approved
0.6277	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4270	Approved
0.6237	Remote Similarity	NPD4269	Approved
0.6226	Remote Similarity	NPD6675	Approved
0.6226	Remote Similarity	NPD5739	Approved
0.6226	Remote Similarity	NPD6402	Approved
0.6226	Remote Similarity	NPD7128	Approved
0.6226	Remote Similarity	NPD4768	Approved
0.6226	Remote Similarity	NPD4767	Approved
0.6222	Remote Similarity	NPD6925	Approved
0.6222	Remote Similarity	NPD5776	Phase 2
0.6214	Remote Similarity	NPD7639	Approved
0.6214	Remote Similarity	NPD7640	Approved
0.6211	Remote Similarity	NPD6893	Approved
0.62	Remote Similarity	NPD5282	Discontinued
0.6196	Remote Similarity	NPD7509	Discontinued
0.6186	Remote Similarity	NPD5208	Approved
0.618	Remote Similarity	NPD6942	Approved
0.618	Remote Similarity	NPD7339	Approved
0.617	Remote Similarity	NPD6110	Phase 1
0.617	Remote Similarity	NPD5362	Discontinued
0.617	Remote Similarity	NPD7154	Phase 3
0.6168	Remote Similarity	NPD5701	Approved
0.6168	Remote Similarity	NPD5697	Approved
0.6163	Remote Similarity	NPD6922	Approved
0.6163	Remote Similarity	NPD6923	Approved
0.6162	Remote Similarity	NPD5693	Phase 1
0.6162	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD7145	Approved
0.6147	Remote Similarity	NPD6371	Approved
0.6139	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5654	Approved
0.6136	Remote Similarity	NPD4732	Discontinued
0.6129	Remote Similarity	NPD6898	Phase 1
0.6129	Remote Similarity	NPD6902	Approved
0.6126	Remote Similarity	NPD4632	Approved
0.6125	Remote Similarity	NPD287	Approved
0.6122	Remote Similarity	NPD6673	Approved
0.6122	Remote Similarity	NPD6904	Approved
0.6122	Remote Similarity	NPD6080	Approved
0.6117	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7638	Approved
0.6111	Remote Similarity	NPD6899	Approved
0.6111	Remote Similarity	NPD6011	Approved
0.6111	Remote Similarity	NPD5128	Approved
0.6111	Remote Similarity	NPD4729	Approved
0.6111	Remote Similarity	NPD4730	Approved
0.6111	Remote Similarity	NPD6686	Approved
0.6111	Remote Similarity	NPD7320	Approved
0.6111	Remote Similarity	NPD6881	Approved
0.6092	Remote Similarity	NPD7144	Approved
0.6092	Remote Similarity	NPD7143	Approved
0.6091	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7750	Discontinued
0.6078	Remote Similarity	NPD7614	Phase 1
0.6064	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7838	Discovery
0.6055	Remote Similarity	NPD6013	Approved
0.6055	Remote Similarity	NPD4061	Clinical (unspecified phase)

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