NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	2.347
LogD:	1.776
LogS:	-1.803
# Rotatable Bonds:	1
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	4.266
Fsp3:	0.733
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:	-4.656
MDCK Permeability:	3.1989031413104385e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.146
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.309
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.744
Plasma Protein Binding (PPB):	53.02276611328125%
Volume Distribution (VD):	0.798
Pgp-substrate:	60.58445739746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.553
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	17.408
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.217
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.326
Maximum Recommended Daily Dose:	0.77
Skin Sensitization:	0.187
Carcinogencity:	0.711
Eye Corrosion:	0.812
Eye Irritation:	0.437
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC308038

Natural Product ID:	NPC308038
*Common Name:**	(+)-(4R,5S,7R,9R)-9Alpha-Hydroxynootkatone
IUPAC Name:	(4R,4aS,6S,8R)-8-hydroxy-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
Synonyms:
Standard InCHIKey:	AHROGQKIGMNGTG-FKGLVLAHSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9(2)11-6-14(17)13-7-12(16)5-10(3)15(13,4)8-11/h7,10-11,14,17H,1,5-6,8H2,2-4H3/t10-,11-,14-,15+/m1/s1
SMILES:	C=C(C)[C@@H]1C[C@H](C2=CC(=O)C[C@@H](C)[C@]2(C)C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1766881
PubChem CID:	11128252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane 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
Others	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	ID50	=	62.7	ug ml-1	PMID[551421]
NPT116	Cell Line	HL-60	Homo sapiens	ID50	=	25.7	ug ml-1	PMID[551421]

☑ 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 NPC308038 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	158
0.1-0.2	1039
0.2-0.3	4617
0.3-0.4	12349
0.4-0.5	11791
0.5-0.6	6835
0.6-0.7	4264
0.7-0.8	1448
0.8-0.85	142
0.85-0.9	38
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC93590
0.9589	High Similarity	NPC263582
0.9459	High Similarity	NPC74995
0.9342	High Similarity	NPC157895
0.9342	High Similarity	NPC104120
0.9342	High Similarity	NPC148685
0.9342	High Similarity	NPC172013
0.9333	High Similarity	NPC62336
0.9211	High Similarity	NPC281138
0.9211	High Similarity	NPC152061
0.92	High Similarity	NPC197659
0.9125	High Similarity	NPC472986
0.9125	High Similarity	NPC472985
0.9079	High Similarity	NPC475994
0.8987	High Similarity	NPC105173
0.8947	High Similarity	NPC257666
0.8947	High Similarity	NPC203403
0.8947	High Similarity	NPC266193
0.8933	High Similarity	NPC114236
0.8919	High Similarity	NPC186042
0.8919	High Similarity	NPC247586
0.8889	High Similarity	NPC472974
0.8889	High Similarity	NPC194417
0.8875	High Similarity	NPC476412
0.8846	High Similarity	NPC471514
0.8816	High Similarity	NPC472305
0.8816	High Similarity	NPC470525
0.8795	High Similarity	NPC472973
0.8795	High Similarity	NPC473999
0.8795	High Similarity	NPC472983
0.8795	High Similarity	NPC309603
0.8765	High Similarity	NPC476426
0.875	High Similarity	NPC64600
0.875	High Similarity	NPC169941
0.875	High Similarity	NPC251475
0.8718	High Similarity	NPC19900
0.8701	High Similarity	NPC34110
0.8701	High Similarity	NPC97377
0.869	High Similarity	NPC134321
0.8659	High Similarity	NPC198761
0.8642	High Similarity	NPC40687
0.8625	High Similarity	NPC38796
0.8625	High Similarity	NPC158411
0.8608	High Similarity	NPC45495
0.8608	High Similarity	NPC2482
0.8608	High Similarity	NPC271104
0.8608	High Similarity	NPC472301
0.859	High Similarity	NPC275494
0.859	High Similarity	NPC471409
0.859	High Similarity	NPC178852
0.859	High Similarity	NPC297996
0.8588	High Similarity	NPC475806
0.8588	High Similarity	NPC116726
0.8588	High Similarity	NPC473998
0.8588	High Similarity	NPC472978
0.8571	High Similarity	NPC473100
0.8571	High Similarity	NPC250621
0.8553	High Similarity	NPC215050
0.8537	High Similarity	NPC470574
0.8537	High Similarity	NPC474853
0.8537	High Similarity	NPC52628
0.8537	High Similarity	NPC179006
0.8537	High Similarity	NPC274724
0.8537	High Similarity	NPC474083
0.8537	High Similarity	NPC471224
0.8519	High Similarity	NPC297398
0.85	High Similarity	NPC121984
0.85	High Similarity	NPC226068
0.85	High Similarity	NPC6663
0.8488	Intermediate Similarity	NPC69454
0.8488	Intermediate Similarity	NPC109305
0.8481	Intermediate Similarity	NPC7232
0.8471	Intermediate Similarity	NPC473099
0.8471	Intermediate Similarity	NPC128672
0.8471	Intermediate Similarity	NPC230332
0.8471	Intermediate Similarity	NPC48010
0.8452	Intermediate Similarity	NPC104560
0.8434	Intermediate Similarity	NPC82979
0.8434	Intermediate Similarity	NPC473226
0.8434	Intermediate Similarity	NPC470955
0.8415	Intermediate Similarity	NPC58841
0.8415	Intermediate Similarity	NPC214043
0.8415	Intermediate Similarity	NPC473246
0.8415	Intermediate Similarity	NPC329043
0.8415	Intermediate Similarity	NPC321187
0.8415	Intermediate Similarity	NPC85774
0.8415	Intermediate Similarity	NPC161423
0.8415	Intermediate Similarity	NPC227064
0.8415	Intermediate Similarity	NPC470812
0.8395	Intermediate Similarity	NPC103486
0.8395	Intermediate Similarity	NPC48362
0.8391	Intermediate Similarity	NPC472977
0.8391	Intermediate Similarity	NPC8993
0.8391	Intermediate Similarity	NPC472976
0.8391	Intermediate Similarity	NPC196227
0.8375	Intermediate Similarity	NPC306095
0.8372	Intermediate Similarity	NPC472975
0.8372	Intermediate Similarity	NPC233116
0.8372	Intermediate Similarity	NPC63748
0.8354	Intermediate Similarity	NPC239098
0.8353	Intermediate Similarity	NPC123912
0.8353	Intermediate Similarity	NPC472970
0.8353	Intermediate Similarity	NPC472971
0.8333	Intermediate Similarity	NPC151622
0.8333	Intermediate Similarity	NPC7629
0.8333	Intermediate Similarity	NPC287079
0.8313	Intermediate Similarity	NPC15807
0.8312	Intermediate Similarity	NPC470299
0.8295	Intermediate Similarity	NPC271195
0.8295	Intermediate Similarity	NPC476245
0.8295	Intermediate Similarity	NPC259286
0.8276	Intermediate Similarity	NPC474736
0.8276	Intermediate Similarity	NPC472930
0.8272	Intermediate Similarity	NPC14151
0.8272	Intermediate Similarity	NPC473420
0.8272	Intermediate Similarity	NPC116797
0.8272	Intermediate Similarity	NPC136150
0.8272	Intermediate Similarity	NPC470298
0.825	Intermediate Similarity	NPC170394
0.825	Intermediate Similarity	NPC229204
0.8235	Intermediate Similarity	NPC158778
0.8235	Intermediate Similarity	NPC472802
0.8235	Intermediate Similarity	NPC471793
0.8235	Intermediate Similarity	NPC474854
0.8235	Intermediate Similarity	NPC328539
0.8235	Intermediate Similarity	NPC471791
0.8235	Intermediate Similarity	NPC471722
0.8228	Intermediate Similarity	NPC61952
0.8228	Intermediate Similarity	NPC165711
0.8228	Intermediate Similarity	NPC325946
0.8214	Intermediate Similarity	NPC469994
0.8214	Intermediate Similarity	NPC31564
0.8214	Intermediate Similarity	NPC158393
0.8214	Intermediate Similarity	NPC145879
0.8214	Intermediate Similarity	NPC72133
0.8214	Intermediate Similarity	NPC327115
0.8214	Intermediate Similarity	NPC179591
0.8214	Intermediate Similarity	NPC476043
0.8214	Intermediate Similarity	NPC474732
0.8214	Intermediate Similarity	NPC474778
0.8214	Intermediate Similarity	NPC474733
0.8214	Intermediate Similarity	NPC94666
0.8214	Intermediate Similarity	NPC322159
0.8205	Intermediate Similarity	NPC476795
0.8202	Intermediate Similarity	NPC249954
0.8202	Intermediate Similarity	NPC117133
0.8193	Intermediate Similarity	NPC227132
0.8193	Intermediate Similarity	NPC165064
0.8193	Intermediate Similarity	NPC237712
0.8193	Intermediate Similarity	NPC472326
0.8182	Intermediate Similarity	NPC474690
0.8182	Intermediate Similarity	NPC29542
0.8182	Intermediate Similarity	NPC201562
0.8182	Intermediate Similarity	NPC323437
0.8182	Intermediate Similarity	NPC299100
0.8171	Intermediate Similarity	NPC151519
0.8171	Intermediate Similarity	NPC212083
0.8158	Intermediate Similarity	NPC34834
0.8148	Intermediate Similarity	NPC472478
0.8148	Intermediate Similarity	NPC476809
0.8148	Intermediate Similarity	NPC281880
0.814	Intermediate Similarity	NPC281524
0.814	Intermediate Similarity	NPC275740
0.814	Intermediate Similarity	NPC2983
0.814	Intermediate Similarity	NPC214387
0.814	Intermediate Similarity	NPC119416
0.814	Intermediate Similarity	NPC86319
0.814	Intermediate Similarity	NPC5509
0.814	Intermediate Similarity	NPC36668
0.814	Intermediate Similarity	NPC118011
0.8133	Intermediate Similarity	NPC117804
0.8133	Intermediate Similarity	NPC96484
0.8125	Intermediate Similarity	NPC198240
0.8125	Intermediate Similarity	NPC253561
0.8125	Intermediate Similarity	NPC80088
0.8118	Intermediate Similarity	NPC58063
0.8118	Intermediate Similarity	NPC141292
0.8118	Intermediate Similarity	NPC272039
0.8118	Intermediate Similarity	NPC475740
0.8118	Intermediate Similarity	NPC136548
0.8118	Intermediate Similarity	NPC312561
0.8118	Intermediate Similarity	NPC220930
0.8111	Intermediate Similarity	NPC253826
0.8101	Intermediate Similarity	NPC180886
0.8101	Intermediate Similarity	NPC76966
0.8101	Intermediate Similarity	NPC186554
0.8101	Intermediate Similarity	NPC469646
0.8095	Intermediate Similarity	NPC70685
0.8095	Intermediate Similarity	NPC476678
0.8095	Intermediate Similarity	NPC79573
0.8095	Intermediate Similarity	NPC133954
0.8095	Intermediate Similarity	NPC469948
0.809	Intermediate Similarity	NPC472932
0.809	Intermediate Similarity	NPC316215
0.809	Intermediate Similarity	NPC180950
0.8072	Intermediate Similarity	NPC110150
0.8072	Intermediate Similarity	NPC49019
0.8072	Intermediate Similarity	NPC66764
0.8068	Intermediate Similarity	NPC115021
0.8052	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 NPC308038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1455
0.2-0.3	3792
0.3-0.4	2513
0.4-0.5	770
0.5-0.6	226
0.6-0.7	202
0.7-0.8	42
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
0.8434	Intermediate Similarity	NPD3618	Phase 1
0.8415	Intermediate Similarity	NPD3666	Approved
0.8415	Intermediate Similarity	NPD3133	Approved
0.8415	Intermediate Similarity	NPD3665	Phase 1
0.8214	Intermediate Similarity	NPD5279	Phase 3
0.8171	Intermediate Similarity	NPD3667	Approved
0.814	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD4519	Discontinued
0.8	Intermediate Similarity	NPD4623	Approved
0.7976	Intermediate Similarity	NPD4786	Approved
0.7955	Intermediate Similarity	NPD6079	Approved
0.7955	Intermediate Similarity	NPD7515	Phase 2
0.7927	Intermediate Similarity	NPD4695	Discontinued
0.7865	Intermediate Similarity	NPD4202	Approved
0.7738	Intermediate Similarity	NPD4223	Phase 3
0.7738	Intermediate Similarity	NPD4221	Approved
0.7727	Intermediate Similarity	NPD4753	Phase 2
0.7609	Intermediate Similarity	NPD4697	Phase 3
0.7609	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5222	Approved
0.7609	Intermediate Similarity	NPD5221	Approved
0.7582	Intermediate Similarity	NPD7748	Approved
0.7579	Intermediate Similarity	NPD5211	Phase 2
0.7558	Intermediate Similarity	NPD4197	Approved
0.7527	Intermediate Similarity	NPD4755	Approved
0.7527	Intermediate Similarity	NPD5173	Approved
0.7471	Intermediate Similarity	NPD5329	Approved
0.7471	Intermediate Similarity	NPD1694	Approved
0.7471	Intermediate Similarity	NPD1696	Phase 3
0.747	Intermediate Similarity	NPD3617	Approved
0.7423	Intermediate Similarity	NPD5141	Approved
0.7386	Intermediate Similarity	NPD5690	Phase 2
0.7386	Intermediate Similarity	NPD4688	Approved
0.7386	Intermediate Similarity	NPD4690	Approved
0.7386	Intermediate Similarity	NPD4138	Approved
0.7386	Intermediate Similarity	NPD4689	Approved
0.7386	Intermediate Similarity	NPD4693	Phase 3
0.7386	Intermediate Similarity	NPD6409	Approved
0.7386	Intermediate Similarity	NPD5205	Approved
0.7386	Intermediate Similarity	NPD7334	Approved
0.7386	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD7146	Approved
0.7386	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4694	Approved
0.7386	Intermediate Similarity	NPD6684	Approved
0.7386	Intermediate Similarity	NPD5280	Approved
0.7386	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD5285	Approved
0.7368	Intermediate Similarity	NPD5286	Approved
0.7368	Intermediate Similarity	NPD4700	Approved
0.7368	Intermediate Similarity	NPD4696	Approved
0.7356	Intermediate Similarity	NPD3668	Phase 3
0.734	Intermediate Similarity	NPD7902	Approved
0.7326	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8264	Approved
0.7312	Intermediate Similarity	NPD4629	Approved
0.7312	Intermediate Similarity	NPD5210	Approved
0.7294	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5223	Approved
0.7262	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD5224	Approved
0.7216	Intermediate Similarity	NPD5225	Approved
0.7216	Intermediate Similarity	NPD4633	Approved
0.7216	Intermediate Similarity	NPD5226	Approved
0.7188	Intermediate Similarity	NPD7640	Approved
0.7188	Intermediate Similarity	NPD7639	Approved
0.7179	Intermediate Similarity	NPD7331	Phase 2
0.7158	Intermediate Similarity	NPD6083	Phase 2
0.7158	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.7128	Intermediate Similarity	NPD5695	Phase 3
0.7125	Intermediate Similarity	NPD4137	Phase 3
0.7097	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD6399	Phase 3
0.7097	Intermediate Similarity	NPD5779	Approved
0.7083	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD7638	Approved
0.7065	Intermediate Similarity	NPD4096	Approved
0.7051	Intermediate Similarity	NPD7341	Phase 2
0.7045	Intermediate Similarity	NPD4788	Approved
0.7037	Intermediate Similarity	NPD4691	Approved
0.7037	Intermediate Similarity	NPD4747	Approved
0.7033	Intermediate Similarity	NPD6672	Approved
0.7033	Intermediate Similarity	NPD5737	Approved
0.7024	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD4768	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.6989	Remote Similarity	NPD5284	Approved
0.6989	Remote Similarity	NPD6411	Approved
0.6989	Remote Similarity	NPD5281	Approved
0.6977	Remote Similarity	NPD7645	Phase 2
0.6977	Remote Similarity	NPD4195	Approved
0.6957	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5276	Approved
0.6931	Remote Similarity	NPD5697	Approved
0.6931	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD3573	Approved
0.6907	Remote Similarity	NPD5696	Approved
0.6905	Remote Similarity	NPD7339	Approved
0.6905	Remote Similarity	NPD6942	Approved
0.6889	Remote Similarity	NPD5363	Approved
0.6889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD368	Approved
0.6882	Remote Similarity	NPD5785	Approved
0.6863	Remote Similarity	NPD5128	Approved
0.6863	Remote Similarity	NPD7320	Approved
0.6863	Remote Similarity	NPD6011	Approved
0.6863	Remote Similarity	NPD5168	Approved
0.6863	Remote Similarity	NPD6899	Approved
0.6863	Remote Similarity	NPD4729	Approved
0.6863	Remote Similarity	NPD4730	Approved
0.6863	Remote Similarity	NPD6881	Approved
0.6848	Remote Similarity	NPD4518	Approved
0.6822	Remote Similarity	NPD7115	Discovery
0.6818	Remote Similarity	NPD4139	Approved
0.6818	Remote Similarity	NPD4692	Approved
0.6796	Remote Similarity	NPD6014	Approved
0.6796	Remote Similarity	NPD6373	Approved
0.6796	Remote Similarity	NPD6013	Approved
0.6796	Remote Similarity	NPD6012	Approved
0.6796	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD5733	Approved
0.6786	Remote Similarity	NPD4687	Approved
0.6786	Remote Similarity	NPD6926	Approved
0.6786	Remote Similarity	NPD6924	Approved
0.6786	Remote Similarity	NPD4058	Approved
0.6782	Remote Similarity	NPD6929	Approved
0.6774	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6101	Approved
0.6765	Remote Similarity	NPD6412	Phase 2
0.6757	Remote Similarity	NPD342	Phase 1
0.6742	Remote Similarity	NPD4270	Approved
0.6742	Remote Similarity	NPD4269	Approved
0.6739	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5133	Approved
0.6731	Remote Similarity	NPD5250	Approved
0.6731	Remote Similarity	NPD7102	Approved
0.6731	Remote Similarity	NPD5249	Phase 3
0.6731	Remote Similarity	NPD5169	Approved
0.6731	Remote Similarity	NPD5248	Approved
0.6731	Remote Similarity	NPD4634	Approved
0.6731	Remote Similarity	NPD5247	Approved
0.6731	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD5135	Approved
0.6731	Remote Similarity	NPD5251	Approved
0.6731	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7290	Approved
0.6711	Remote Similarity	NPD287	Approved
0.6707	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7525	Registered
0.6705	Remote Similarity	NPD6930	Phase 2
0.6705	Remote Similarity	NPD6931	Approved
0.6699	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6632	Remote Similarity	NPD5693	Phase 1
0.6628	Remote Similarity	NPD6933	Approved
0.6625	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD8297	Approved
0.6598	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6673	Approved
0.6596	Remote Similarity	NPD6080	Approved
0.6596	Remote Similarity	NPD6904	Approved
0.6585	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5290	Discontinued
0.6552	Remote Similarity	NPD5776	Phase 2
0.6552	Remote Similarity	NPD6925	Approved
0.6548	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4632	Approved
0.6535	Remote Similarity	NPD7632	Discontinued
0.6531	Remote Similarity	NPD7614	Phase 1
0.6526	Remote Similarity	NPD5207	Approved
0.6526	Remote Similarity	NPD5692	Phase 3

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