NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.15
Volume:	228.599
LogP:	2.518
LogD:	2.475
LogS:	-3.298
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	4.151
Fsp3:	0.769
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:	-4.642
MDCK Permeability:	2.3311329641728662e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.146
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	83.8790054321289%
Volume Distribution (VD):	1.261
Pgp-substrate:	7.062228679656982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.399
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.164
CYP2C9-substrate:	0.613
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.39
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.494

ADMET: Excretion

Clearance (CL):	6.171
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.699
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.669
Carcinogencity:	0.123
Eye Corrosion:	0.346
Eye Irritation:	0.943
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC233352

Natural Product ID:	NPC233352
*Common Name:**	(+)-(1R,6S,9R)-1-Hydroxyl-6-Isopropyl-9-Methylbicyclo[4.3.0]Non-4-En-3-One
IUPAC Name:	(4S,7R,7aR)-7a-hydroxy-7-methyl-4-propan-2-yl-4,5,6,7-tetrahydro-1H-inden-2-one
Synonyms:
Standard InCHIKey:	LSRLIQNNCDCOJG-SUZMYJTESA-N
Standard InCHI:	InChI=1S/C13H20O2/c1-8(2)11-5-4-9(3)13(15)7-10(14)6-12(11)13/h6,8-9,11,15H,4-5,7H2,1-3H3/t9-,11+,13-/m1/s1
SMILES:	O=C1C=C2[C@](C1)(O)[C@H](C)CC[C@H]2C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL299909
PubChem CID:	11506718
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO29315	Dictyopteris divaricata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497933]
NPO29315	Dictyopteris divaricata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180804]
NPO29315	Dictyopteris divaricata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989516]
NPO29315	Dictyopteris divaricata	Species	Dictyotaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[449478]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[449478]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[449478]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[449478]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[449478]

☑ 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 NPC233352 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	153
0.1-0.2	1186
0.2-0.3	5414
0.3-0.4	12871
0.4-0.5	12282
0.5-0.6	7106
0.6-0.7	3234
0.7-0.8	419
0.8-0.85	18
0.85-0.9	7
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC824
1.0	High Similarity	NPC138492
0.925	High Similarity	NPC476043
0.9221	High Similarity	NPC74445
0.9221	High Similarity	NPC287817
0.8831	High Similarity	NPC34110
0.8701	High Similarity	NPC472305
0.8684	High Similarity	NPC7382
0.8481	Intermediate Similarity	NPC19443
0.8481	Intermediate Similarity	NPC207772
0.8462	Intermediate Similarity	NPC7629
0.8462	Intermediate Similarity	NPC151622
0.8354	Intermediate Similarity	NPC266193
0.8354	Intermediate Similarity	NPC257666
0.8333	Intermediate Similarity	NPC89374
0.8272	Intermediate Similarity	NPC472301
0.8228	Intermediate Similarity	NPC76966
0.8228	Intermediate Similarity	NPC186554
0.8214	Intermediate Similarity	NPC179006
0.8214	Intermediate Similarity	NPC474853
0.8171	Intermediate Similarity	NPC226068
0.8148	Intermediate Similarity	NPC476624
0.8148	Intermediate Similarity	NPC472013
0.8118	Intermediate Similarity	NPC194417
0.8077	Intermediate Similarity	NPC247586
0.8072	Intermediate Similarity	NPC256750
0.8072	Intermediate Similarity	NPC20262
0.8049	Intermediate Similarity	NPC157895
0.8049	Intermediate Similarity	NPC104120
0.8049	Intermediate Similarity	NPC45495
0.8049	Intermediate Similarity	NPC148685
0.8025	Intermediate Similarity	NPC471409
0.8025	Intermediate Similarity	NPC476627
0.8025	Intermediate Similarity	NPC275494
0.8	Intermediate Similarity	NPC182848
0.7931	Intermediate Similarity	NPC474854
0.7927	Intermediate Similarity	NPC308038
0.7927	Intermediate Similarity	NPC7232
0.7907	Intermediate Similarity	NPC472869
0.7857	Intermediate Similarity	NPC193347
0.7841	Intermediate Similarity	NPC472971
0.7841	Intermediate Similarity	NPC472970
0.7831	Intermediate Similarity	NPC172013
0.7805	Intermediate Similarity	NPC80088
0.7805	Intermediate Similarity	NPC253561
0.7791	Intermediate Similarity	NPC70685
0.7791	Intermediate Similarity	NPC476628
0.7778	Intermediate Similarity	NPC472871
0.7778	Intermediate Similarity	NPC263582
0.7765	Intermediate Similarity	NPC297398
0.7753	Intermediate Similarity	NPC230332
0.7738	Intermediate Similarity	NPC473217
0.7727	Intermediate Similarity	NPC72397
0.7727	Intermediate Similarity	NPC471791
0.7727	Intermediate Similarity	NPC471793
0.7727	Intermediate Similarity	NPC48107
0.7727	Intermediate Similarity	NPC472870
0.7711	Intermediate Similarity	NPC301769
0.7711	Intermediate Similarity	NPC170394
0.7711	Intermediate Similarity	NPC281138
0.7711	Intermediate Similarity	NPC32758
0.7692	Intermediate Similarity	NPC299100
0.7683	Intermediate Similarity	NPC197659
0.7683	Intermediate Similarity	NPC97377
0.7674	Intermediate Similarity	NPC144258
0.7674	Intermediate Similarity	NPC19849
0.7674	Intermediate Similarity	NPC472865
0.7674	Intermediate Similarity	NPC472864
0.7674	Intermediate Similarity	NPC248758
0.7667	Intermediate Similarity	NPC475806
0.7662	Intermediate Similarity	NPC263161
0.7654	Intermediate Similarity	NPC77501
0.7647	Intermediate Similarity	NPC469325
0.7647	Intermediate Similarity	NPC93590
0.764	Intermediate Similarity	NPC472676
0.764	Intermediate Similarity	NPC309603
0.764	Intermediate Similarity	NPC473999
0.764	Intermediate Similarity	NPC472688
0.7625	Intermediate Similarity	NPC35656
0.7619	Intermediate Similarity	NPC476809
0.7614	Intermediate Similarity	NPC136948
0.7614	Intermediate Similarity	NPC471792
0.7609	Intermediate Similarity	NPC259286
0.7609	Intermediate Similarity	NPC180950
0.7609	Intermediate Similarity	NPC271195
0.759	Intermediate Similarity	NPC62336
0.759	Intermediate Similarity	NPC297996
0.7586	Intermediate Similarity	NPC79573
0.7582	Intermediate Similarity	NPC69454
0.7579	Intermediate Similarity	NPC282524
0.7561	Intermediate Similarity	NPC239758
0.7558	Intermediate Similarity	NPC97913
0.7558	Intermediate Similarity	NPC64600
0.7558	Intermediate Similarity	NPC477373
0.7556	Intermediate Similarity	NPC472866
0.7556	Intermediate Similarity	NPC48010
0.7556	Intermediate Similarity	NPC134321
0.7529	Intermediate Similarity	NPC171665
0.7529	Intermediate Similarity	NPC119229
0.7529	Intermediate Similarity	NPC477372
0.7529	Intermediate Similarity	NPC44963
0.7529	Intermediate Similarity	NPC472684
0.7528	Intermediate Similarity	NPC58271
0.7528	Intermediate Similarity	NPC471941
0.7528	Intermediate Similarity	NPC117122
0.7527	Intermediate Similarity	NPC249954
0.7527	Intermediate Similarity	NPC117133
0.75	Intermediate Similarity	NPC84185
0.75	Intermediate Similarity	NPC198761
0.75	Intermediate Similarity	NPC472974
0.75	Intermediate Similarity	NPC106309
0.75	Intermediate Similarity	NPC29328
0.75	Intermediate Similarity	NPC215843
0.75	Intermediate Similarity	NPC472488
0.75	Intermediate Similarity	NPC472986
0.75	Intermediate Similarity	NPC472479
0.75	Intermediate Similarity	NPC84790
0.75	Intermediate Similarity	NPC53685
0.75	Intermediate Similarity	NPC229204
0.75	Intermediate Similarity	NPC66677
0.75	Intermediate Similarity	NPC472985
0.75	Intermediate Similarity	NPC471890
0.75	Intermediate Similarity	NPC8993
0.75	Intermediate Similarity	NPC474690
0.75	Intermediate Similarity	NPC470955
0.7474	Intermediate Similarity	NPC154072
0.7473	Intermediate Similarity	NPC473998
0.7473	Intermediate Similarity	NPC233116
0.7473	Intermediate Similarity	NPC63748
0.7473	Intermediate Similarity	NPC116726
0.7471	Intermediate Similarity	NPC251170
0.7471	Intermediate Similarity	NPC472480
0.7471	Intermediate Similarity	NPC58841
0.7471	Intermediate Similarity	NPC164577
0.7471	Intermediate Similarity	NPC161423
0.7471	Intermediate Similarity	NPC321187
0.7471	Intermediate Similarity	NPC329043
0.7471	Intermediate Similarity	NPC227064
0.7471	Intermediate Similarity	NPC476412
0.747	Intermediate Similarity	NPC472014
0.747	Intermediate Similarity	NPC74995
0.747	Intermediate Similarity	NPC132542
0.747	Intermediate Similarity	NPC61952
0.7447	Intermediate Similarity	NPC474938
0.7447	Intermediate Similarity	NPC477267
0.7447	Intermediate Similarity	NPC472690
0.7447	Intermediate Similarity	NPC477268
0.7447	Intermediate Similarity	NPC472689
0.7447	Intermediate Similarity	NPC474785
0.7444	Intermediate Similarity	NPC36668
0.7444	Intermediate Similarity	NPC472983
0.7444	Intermediate Similarity	NPC118011
0.7444	Intermediate Similarity	NPC170775
0.7444	Intermediate Similarity	NPC472973
0.7444	Intermediate Similarity	NPC262043
0.7444	Intermediate Similarity	NPC119416
0.7444	Intermediate Similarity	NPC2983
0.7442	Intermediate Similarity	NPC133844
0.7442	Intermediate Similarity	NPC92226
0.7439	Intermediate Similarity	NPC476795
0.7439	Intermediate Similarity	NPC39362
0.7436	Intermediate Similarity	NPC278895
0.7423	Intermediate Similarity	NPC168575
0.7423	Intermediate Similarity	NPC72151
0.7423	Intermediate Similarity	NPC475050
0.7419	Intermediate Similarity	NPC280725
0.7416	Intermediate Similarity	NPC141292
0.7416	Intermediate Similarity	NPC171722
0.7412	Intermediate Similarity	NPC469637
0.7412	Intermediate Similarity	NPC271104
0.7412	Intermediate Similarity	NPC306095
0.7407	Intermediate Similarity	NPC300940
0.7407	Intermediate Similarity	NPC275098
0.7391	Intermediate Similarity	NPC131840
0.7391	Intermediate Similarity	NPC472930
0.7391	Intermediate Similarity	NPC109305
0.7391	Intermediate Similarity	NPC477520
0.7386	Intermediate Similarity	NPC474083
0.7386	Intermediate Similarity	NPC471224
0.7386	Intermediate Similarity	NPC269638
0.7386	Intermediate Similarity	NPC470574
0.7381	Intermediate Similarity	NPC478122
0.7381	Intermediate Similarity	NPC198240
0.7381	Intermediate Similarity	NPC475994
0.7381	Intermediate Similarity	NPC169095
0.7381	Intermediate Similarity	NPC178852
0.7381	Intermediate Similarity	NPC179028
0.7381	Intermediate Similarity	NPC172066
0.7368	Intermediate Similarity	NPC316598
0.7363	Intermediate Similarity	NPC126993
0.7363	Intermediate Similarity	NPC77337
0.7363	Intermediate Similarity	NPC85173
0.7363	Intermediate Similarity	NPC128672
0.7356	Intermediate Similarity	NPC470165
0.7356	Intermediate Similarity	NPC110150
0.7356	Intermediate Similarity	NPC49019
0.7356	Intermediate Similarity	NPC251475
0.7356	Intermediate Similarity	NPC215893
0.7356	Intermediate Similarity	NPC472492
0.7356	Intermediate Similarity	NPC66764

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 NPC233352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1679
0.2-0.3	3912
0.3-0.4	2349
0.4-0.5	660
0.5-0.6	259
0.6-0.7	133
0.7-0.8	11
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
0.8118	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4519	Discontinued
0.7907	Intermediate Similarity	NPD4623	Approved
0.7857	Intermediate Similarity	NPD4221	Approved
0.7857	Intermediate Similarity	NPD4223	Phase 3
0.7674	Intermediate Similarity	NPD4197	Approved
0.7586	Intermediate Similarity	NPD5329	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD5280	Approved
0.7471	Intermediate Similarity	NPD3665	Phase 1
0.7471	Intermediate Similarity	NPD3133	Approved
0.7471	Intermediate Similarity	NPD3666	Approved
0.7391	Intermediate Similarity	NPD4202	Approved
0.7253	Intermediate Similarity	NPD5328	Approved
0.7253	Intermediate Similarity	NPD4753	Phase 2
0.7176	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7097	Intermediate Similarity	NPD5281	Approved
0.7097	Intermediate Similarity	NPD5284	Approved
0.7097	Intermediate Similarity	NPD6079	Approved
0.7093	Intermediate Similarity	NPD4195	Approved
0.7089	Intermediate Similarity	NPD7331	Phase 2
0.7083	Intermediate Similarity	NPD4755	Approved
0.7045	Intermediate Similarity	NPD3667	Approved
0.7011	Intermediate Similarity	NPD4695	Discontinued
0.7	Intermediate Similarity	NPD1696	Phase 3
0.7	Intermediate Similarity	NPD5141	Approved
0.7	Intermediate Similarity	NPD5363	Approved
0.6989	Remote Similarity	NPD4096	Approved
0.6962	Remote Similarity	NPD7341	Phase 2
0.6939	Remote Similarity	NPD4696	Approved
0.6939	Remote Similarity	NPD5286	Approved
0.6939	Remote Similarity	NPD4700	Approved
0.6939	Remote Similarity	NPD5285	Approved
0.6932	Remote Similarity	NPD4139	Approved
0.6932	Remote Similarity	NPD4692	Approved
0.6923	Remote Similarity	NPD5279	Phase 3
0.6889	Remote Similarity	NPD4786	Approved
0.6875	Remote Similarity	NPD5210	Approved
0.6875	Remote Similarity	NPD4629	Approved
0.6875	Remote Similarity	NPD5695	Phase 3
0.6869	Remote Similarity	NPD5223	Approved
0.6854	Remote Similarity	NPD4270	Approved
0.6854	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4269	Approved
0.6842	Remote Similarity	NPD5133	Approved
0.6829	Remote Similarity	NPD4137	Phase 3
0.6804	Remote Similarity	NPD4697	Phase 3
0.6804	Remote Similarity	NPD5222	Approved
0.6804	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5221	Approved
0.68	Remote Similarity	NPD5225	Approved
0.68	Remote Similarity	NPD5226	Approved
0.68	Remote Similarity	NPD5224	Approved
0.68	Remote Similarity	NPD4633	Approved
0.6778	Remote Similarity	NPD4788	Approved
0.6774	Remote Similarity	NPD4518	Approved
0.6774	Remote Similarity	NPD5208	Approved
0.6771	Remote Similarity	NPD6001	Approved
0.6747	Remote Similarity	NPD4747	Approved
0.6747	Remote Similarity	NPD4691	Approved
0.6739	Remote Similarity	NPD5330	Approved
0.6739	Remote Similarity	NPD6409	Approved
0.6739	Remote Similarity	NPD7334	Approved
0.6739	Remote Similarity	NPD6684	Approved
0.6739	Remote Similarity	NPD7146	Approved
0.6739	Remote Similarity	NPD7521	Approved
0.6737	Remote Similarity	NPD7515	Phase 2
0.6737	Remote Similarity	NPD5693	Phase 1
0.6735	Remote Similarity	NPD5173	Approved
0.6735	Remote Similarity	NPD6084	Phase 2
0.6735	Remote Similarity	NPD6083	Phase 2
0.6733	Remote Similarity	NPD5175	Approved
0.6733	Remote Similarity	NPD4754	Approved
0.6733	Remote Similarity	NPD5174	Approved
0.6702	Remote Similarity	NPD6673	Approved
0.6702	Remote Similarity	NPD6080	Approved
0.6702	Remote Similarity	NPD6904	Approved
0.6701	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6632	Remote Similarity	NPD5785	Approved
0.6632	Remote Similarity	NPD5207	Approved
0.6632	Remote Similarity	NPD5692	Phase 3
0.663	Remote Similarity	NPD1694	Approved
0.6629	Remote Similarity	NPD4252	Approved
0.6606	Remote Similarity	NPD7115	Discovery
0.6602	Remote Similarity	NPD5739	Approved
0.6602	Remote Similarity	NPD6675	Approved
0.6602	Remote Similarity	NPD7128	Approved
0.6602	Remote Similarity	NPD4768	Approved
0.6602	Remote Similarity	NPD6402	Approved
0.6602	Remote Similarity	NPD4767	Approved
0.66	Remote Similarity	NPD7639	Approved
0.66	Remote Similarity	NPD7640	Approved
0.6598	Remote Similarity	NPD7748	Approved
0.6596	Remote Similarity	NPD6903	Approved
0.6596	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5362	Discontinued
0.6562	Remote Similarity	NPD6050	Approved
0.6562	Remote Similarity	NPD5694	Approved
0.6559	Remote Similarity	NPD6098	Approved
0.6559	Remote Similarity	NPD5786	Approved
0.6556	Remote Similarity	NPD5369	Approved
0.6538	Remote Similarity	NPD5701	Approved
0.6538	Remote Similarity	NPD5697	Approved
0.6522	Remote Similarity	NPD3668	Phase 3
0.6512	Remote Similarity	NPD4058	Approved
0.6512	Remote Similarity	NPD4687	Approved
0.6512	Remote Similarity	NPD5733	Approved
0.65	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD7638	Approved
0.6484	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5128	Approved
0.6476	Remote Similarity	NPD4730	Approved
0.6476	Remote Similarity	NPD6899	Approved
0.6476	Remote Similarity	NPD6011	Approved
0.6476	Remote Similarity	NPD6881	Approved
0.6476	Remote Similarity	NPD7320	Approved
0.6476	Remote Similarity	NPD4729	Approved
0.6471	Remote Similarity	NPD4243	Approved
0.6471	Remote Similarity	NPD5276	Approved
0.6471	Remote Similarity	NPD5091	Approved
0.6436	Remote Similarity	NPD6404	Discontinued
0.6429	Remote Similarity	NPD5282	Discontinued
0.6421	Remote Similarity	NPD5737	Approved
0.6421	Remote Similarity	NPD6672	Approved
0.6415	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD6012	Approved
0.6415	Remote Similarity	NPD6014	Approved
0.6415	Remote Similarity	NPD6013	Approved
0.6415	Remote Similarity	NPD6372	Approved
0.6404	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7902	Approved
0.6375	Remote Similarity	NPD368	Approved
0.6355	Remote Similarity	NPD5248	Approved
0.6355	Remote Similarity	NPD5135	Approved
0.6355	Remote Similarity	NPD5249	Phase 3
0.6355	Remote Similarity	NPD5247	Approved
0.6355	Remote Similarity	NPD7290	Approved
0.6355	Remote Similarity	NPD5251	Approved
0.6355	Remote Similarity	NPD6883	Approved
0.6355	Remote Similarity	NPD5250	Approved
0.6355	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7102	Approved
0.6355	Remote Similarity	NPD5169	Approved
0.6354	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5778	Approved
0.6327	Remote Similarity	NPD5779	Approved
0.6327	Remote Similarity	NPD6399	Phase 3
0.6322	Remote Similarity	NPD4784	Approved
0.6322	Remote Similarity	NPD4785	Approved
0.631	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6649	Approved
0.6296	Remote Similarity	NPD6847	Approved
0.6296	Remote Similarity	NPD8130	Phase 1
0.6296	Remote Similarity	NPD6869	Approved
0.6296	Remote Similarity	NPD5215	Approved
0.6296	Remote Similarity	NPD5217	Approved
0.6296	Remote Similarity	NPD6617	Approved
0.6296	Remote Similarity	NPD6650	Approved
0.6296	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5127	Approved
0.6296	Remote Similarity	NPD5216	Approved
0.6277	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4821	Approved
0.6264	Remote Similarity	NPD4819	Approved
0.6264	Remote Similarity	NPD7525	Registered
0.6264	Remote Similarity	NPD4822	Approved
0.6264	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4190	Phase 3
0.625	Remote Similarity	NPD5275	Approved
0.6239	Remote Similarity	NPD8297	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6237	Remote Similarity	NPD7154	Phase 3
0.6203	Remote Similarity	NPD287	Approved
0.62	Remote Similarity	NPD5654	Approved
0.62	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4632	Approved
0.618	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5168	Approved
0.6146	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6054	Approved
0.614	Remote Similarity	NPD6059	Approved
0.614	Remote Similarity	NPD6319	Approved
0.6132	Remote Similarity	NPD6008	Approved
0.6126	Remote Similarity	NPD5167	Approved
0.6118	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5360	Phase 3
0.61	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7900	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