NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	2.107
LogD:	0.833
LogS:	-2.477
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	4.29
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.016
MDCK Permeability:	2.425034654152114e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.555
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	66.27091217041016%
Volume Distribution (VD):	0.27
Pgp-substrate:	27.776981353759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.375
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	4.698
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.369
Skin Sensitization:	0.907
Carcinogencity:	0.801
Eye Corrosion:	0.959
Eye Irritation:	0.981
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC97377

Natural Product ID:	NPC97377
*Common Name:**	Tessaric Acid
IUPAC Name:	2-[(2R,8S,8aR)-8,8a-dimethyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalen-2-yl]prop-2-enoic acid
Synonyms:	Tessaric acid
Standard InCHIKey:	GAWKUNMREBFQOL-ZVWUFJHRSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-6-13(16)7-12-5-4-11(8-15(9,12)3)10(2)14(17)18/h7,9,11H,2,4-6,8H2,1,3H3,(H,17,18)/t9-,11+,15+/m0/s1
SMILES:	O=C1C[C@H](C)[C@@]2(C(=C1)CC[C@H](C2)C(=C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL187784
PubChem CID:	14527134
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
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50031a011]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18303850]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681481]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19344127]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21902175]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26000707]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32880179]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11489	Primula viscosa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11489	Primula viscosa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16644	Ormosia jamaicensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11489	Primula viscosa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11489	Primula viscosa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18695	Citrus limetta	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19045	Solenopsis geminata	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13918	Sinularia rigida	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13328	Bridelia balansae	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16644	Ormosia jamaicensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17051	Bursaphelenchus xylophilus	Species	Aphelenchoididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18369	Stizolophus balsamita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13536	Odontoschisma denudatum	Species	Cephaloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17664	Mucor plumbeus	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17172	Euphorbia hermentiana	Species	Euphorbiaceae	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
GI50	12
Others	2

Activity Type	# Activity
Cell Line	12
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	4000.0	nM	PMID[464814]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	4000.0	nM	PMID[464814]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	=	4000.0	nM	PMID[464814]
NPT179	Cell Line	A2780	Homo sapiens	GI50	=	4000.0	nM	PMID[464814]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	>	100000.0	nM	PMID[464814]
NPT396	Cell Line	T47D	Homo sapiens	GI50	>	100000.0	nM	PMID[464814]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	>	100000.0	nM	PMID[464814]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	>	100000.0	nM	PMID[464814]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	>	100000.0	nM	PMID[464814]
NPT179	Cell Line	A2780	Homo sapiens	GI50	>	100000.0	nM	PMID[464814]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	4000.0	nM	PMID[464814]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	=	4000.0	nM	PMID[464814]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ulcerative index	=	4.62	n.a.	PMID[464813]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition of damage	=	5.0	%	PMID[464813]

☑ 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 NPC97377 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	155
0.1-0.2	1067
0.2-0.3	5355
0.3-0.4	14097
0.4-0.5	10289
0.5-0.6	6784
0.6-0.7	3679
0.7-0.8	1097
0.8-0.85	127
0.85-0.9	34
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC476795
0.9189	High Similarity	NPC165711
0.9167	High Similarity	NPC35656
0.9067	High Similarity	NPC74410
0.9067	High Similarity	NPC198240
0.9067	High Similarity	NPC62336
0.9054	High Similarity	NPC180886
0.9054	High Similarity	NPC263582
0.8974	High Similarity	NPC49019
0.8961	High Similarity	NPC278459
0.8933	High Similarity	NPC266193
0.8933	High Similarity	NPC61952
0.8933	High Similarity	NPC257666
0.8846	High Similarity	NPC302661
0.8846	High Similarity	NPC238991
0.8816	High Similarity	NPC275494
0.8816	High Similarity	NPC179028
0.8816	High Similarity	NPC471409
0.8784	High Similarity	NPC213223
0.8767	High Similarity	NPC21944
0.8765	High Similarity	NPC476409
0.8734	High Similarity	NPC97913
0.8734	High Similarity	NPC102197
0.8718	High Similarity	NPC471898
0.8718	High Similarity	NPC477372
0.8718	High Similarity	NPC90055
0.8701	High Similarity	NPC308038
0.8667	High Similarity	NPC476346
0.8659	High Similarity	NPC48107
0.8659	High Similarity	NPC72397
0.8649	High Similarity	NPC247586
0.8649	High Similarity	NPC109576
0.8649	High Similarity	NPC56747
0.8649	High Similarity	NPC180015
0.8649	High Similarity	NPC130016
0.863	High Similarity	NPC235586
0.8625	High Similarity	NPC472865
0.8625	High Similarity	NPC164577
0.859	High Similarity	NPC271104
0.8571	High Similarity	NPC59436
0.8554	High Similarity	NPC262043
0.8553	High Similarity	NPC470525
0.8553	High Similarity	NPC472305
0.8537	High Similarity	NPC136948
0.8533	High Similarity	NPC283908
0.8533	High Similarity	NPC183503
0.8533	High Similarity	NPC161923
0.8533	High Similarity	NPC103958
0.8519	High Similarity	NPC29447
0.8519	High Similarity	NPC474537
0.8514	High Similarity	NPC160817
0.8514	High Similarity	NPC133253
0.85	High Similarity	NPC105803
0.8462	Intermediate Similarity	NPC477371
0.8442	Intermediate Similarity	NPC34110
0.8442	Intermediate Similarity	NPC74995
0.8442	Intermediate Similarity	NPC472300
0.8421	Intermediate Similarity	NPC39362
0.8421	Intermediate Similarity	NPC472327
0.8421	Intermediate Similarity	NPC279666
0.8421	Intermediate Similarity	NPC192540
0.8415	Intermediate Similarity	NPC472869
0.8395	Intermediate Similarity	NPC19849
0.8395	Intermediate Similarity	NPC248758
0.8395	Intermediate Similarity	NPC476412
0.8395	Intermediate Similarity	NPC472864
0.8395	Intermediate Similarity	NPC96095
0.8375	Intermediate Similarity	NPC93590
0.8375	Intermediate Similarity	NPC320514
0.8354	Intermediate Similarity	NPC45495
0.8354	Intermediate Similarity	NPC172013
0.8354	Intermediate Similarity	NPC476809
0.8354	Intermediate Similarity	NPC26139
0.8354	Intermediate Similarity	NPC108955
0.8353	Intermediate Similarity	NPC204341
0.8333	Intermediate Similarity	NPC118011
0.8333	Intermediate Similarity	NPC189485
0.8333	Intermediate Similarity	NPC169095
0.8333	Intermediate Similarity	NPC239098
0.8333	Intermediate Similarity	NPC5509
0.8333	Intermediate Similarity	NPC36668
0.8333	Intermediate Similarity	NPC321514
0.8333	Intermediate Similarity	NPC475994
0.8312	Intermediate Similarity	NPC7629
0.8312	Intermediate Similarity	NPC309399
0.8312	Intermediate Similarity	NPC69143
0.8312	Intermediate Similarity	NPC186554
0.8312	Intermediate Similarity	NPC76966
0.8312	Intermediate Similarity	NPC151622
0.8293	Intermediate Similarity	NPC474680
0.8289	Intermediate Similarity	NPC301065
0.8289	Intermediate Similarity	NPC237591
0.8289	Intermediate Similarity	NPC241854
0.8289	Intermediate Similarity	NPC3753
0.8289	Intermediate Similarity	NPC251970
0.8289	Intermediate Similarity	NPC46610
0.8289	Intermediate Similarity	NPC476046
0.8289	Intermediate Similarity	NPC18819
0.8272	Intermediate Similarity	NPC297398
0.8267	Intermediate Similarity	NPC84790
0.8256	Intermediate Similarity	NPC476416
0.825	Intermediate Similarity	NPC263272
0.825	Intermediate Similarity	NPC226068
0.825	Intermediate Similarity	NPC267691
0.825	Intermediate Similarity	NPC162632
0.825	Intermediate Similarity	NPC201912
0.825	Intermediate Similarity	NPC40228
0.825	Intermediate Similarity	NPC38350
0.825	Intermediate Similarity	NPC55869
0.825	Intermediate Similarity	NPC274050
0.825	Intermediate Similarity	NPC147066
0.8235	Intermediate Similarity	NPC476437
0.8235	Intermediate Similarity	NPC476369
0.8228	Intermediate Similarity	NPC152061
0.8228	Intermediate Similarity	NPC7232
0.8228	Intermediate Similarity	NPC170394
0.8228	Intermediate Similarity	NPC192329
0.8228	Intermediate Similarity	NPC231431
0.8214	Intermediate Similarity	NPC117122
0.8214	Intermediate Similarity	NPC472870
0.8214	Intermediate Similarity	NPC104560
0.8205	Intermediate Similarity	NPC471897
0.8205	Intermediate Similarity	NPC471899
0.8205	Intermediate Similarity	NPC197659
0.8205	Intermediate Similarity	NPC107039
0.8193	Intermediate Similarity	NPC194417
0.8193	Intermediate Similarity	NPC472974
0.8193	Intermediate Similarity	NPC186975
0.8182	Intermediate Similarity	NPC476844
0.8182	Intermediate Similarity	NPC114236
0.8171	Intermediate Similarity	NPC165064
0.8158	Intermediate Similarity	NPC472813
0.8148	Intermediate Similarity	NPC472239
0.8148	Intermediate Similarity	NPC3511
0.8148	Intermediate Similarity	NPC103486
0.8148	Intermediate Similarity	NPC260956
0.8148	Intermediate Similarity	NPC251779
0.8148	Intermediate Similarity	NPC69101
0.8148	Intermediate Similarity	NPC142253
0.8148	Intermediate Similarity	NPC133391
0.8148	Intermediate Similarity	NPC472867
0.814	Intermediate Similarity	NPC474018
0.814	Intermediate Similarity	NPC473986
0.8125	Intermediate Similarity	NPC104120
0.8125	Intermediate Similarity	NPC157895
0.8125	Intermediate Similarity	NPC472301
0.8125	Intermediate Similarity	NPC2482
0.8125	Intermediate Similarity	NPC37038
0.8125	Intermediate Similarity	NPC148685
0.8118	Intermediate Similarity	NPC477973
0.8101	Intermediate Similarity	NPC260385
0.8101	Intermediate Similarity	NPC280654
0.8101	Intermediate Similarity	NPC207772
0.8101	Intermediate Similarity	NPC110094
0.8095	Intermediate Similarity	NPC236618
0.8082	Intermediate Similarity	NPC322035
0.8082	Intermediate Similarity	NPC100719
0.8082	Intermediate Similarity	NPC166791
0.8077	Intermediate Similarity	NPC40353
0.8077	Intermediate Similarity	NPC19907
0.8077	Intermediate Similarity	NPC89294
0.8072	Intermediate Similarity	NPC189311
0.8072	Intermediate Similarity	NPC65661
0.8072	Intermediate Similarity	NPC142649
0.8072	Intermediate Similarity	NPC476426
0.8072	Intermediate Similarity	NPC86316
0.8072	Intermediate Similarity	NPC106416
0.8072	Intermediate Similarity	NPC52628
0.8049	Intermediate Similarity	NPC168188
0.8049	Intermediate Similarity	NPC470015
0.8049	Intermediate Similarity	NPC477373
0.8049	Intermediate Similarity	NPC69279
0.8049	Intermediate Similarity	NPC70834
0.8049	Intermediate Similarity	NPC83569
0.8046	Intermediate Similarity	NPC131840
0.8046	Intermediate Similarity	NPC115021
0.8026	Intermediate Similarity	NPC288667
0.8026	Intermediate Similarity	NPC29328
0.8025	Intermediate Similarity	NPC327002
0.8025	Intermediate Similarity	NPC225515
0.8025	Intermediate Similarity	NPC473217
0.8025	Intermediate Similarity	NPC475665
0.8025	Intermediate Similarity	NPC116797
0.8025	Intermediate Similarity	NPC44963
0.8025	Intermediate Similarity	NPC473420
0.8025	Intermediate Similarity	NPC472684
0.8025	Intermediate Similarity	NPC121984
0.8025	Intermediate Similarity	NPC142244
0.8023	Intermediate Similarity	NPC472866
0.8023	Intermediate Similarity	NPC51486
0.8	Intermediate Similarity	NPC327674
0.8	Intermediate Similarity	NPC199595
0.8	Intermediate Similarity	NPC16394
0.8	Intermediate Similarity	NPC19900
0.8	Intermediate Similarity	NPC473229
0.8	Intermediate Similarity	NPC281138
0.8	Intermediate Similarity	NPC67608
0.7978	Intermediate Similarity	NPC472941
0.7978	Intermediate Similarity	NPC456
0.7976	Intermediate Similarity	NPC472986

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 NPC97377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1531
0.2-0.3	3812
0.3-0.4	2434
0.4-0.5	731
0.5-0.6	292
0.6-0.7	150
0.7-0.8	45
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
0.8354	Intermediate Similarity	NPD4695	Discontinued
0.7976	Intermediate Similarity	NPD4623	Approved
0.7976	Intermediate Similarity	NPD4519	Discontinued
0.7927	Intermediate Similarity	NPD4223	Phase 3
0.7927	Intermediate Similarity	NPD4221	Approved
0.7765	Intermediate Similarity	NPD5690	Phase 2
0.7738	Intermediate Similarity	NPD4197	Approved
0.7738	Intermediate Similarity	NPD3133	Approved
0.7738	Intermediate Similarity	NPD3665	Phase 1
0.7738	Intermediate Similarity	NPD3666	Approved
0.7727	Intermediate Similarity	NPD7515	Phase 2
0.7727	Intermediate Similarity	NPD5284	Approved
0.7727	Intermediate Similarity	NPD5281	Approved
0.7711	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3573	Approved
0.7654	Intermediate Similarity	NPD3617	Approved
0.7647	Intermediate Similarity	NPD5329	Approved
0.7558	Intermediate Similarity	NPD4688	Approved
0.7558	Intermediate Similarity	NPD6409	Approved
0.7558	Intermediate Similarity	NPD4138	Approved
0.7558	Intermediate Similarity	NPD7521	Approved
0.7558	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4690	Approved
0.7558	Intermediate Similarity	NPD4689	Approved
0.7558	Intermediate Similarity	NPD5280	Approved
0.7558	Intermediate Similarity	NPD3618	Phase 1
0.7558	Intermediate Similarity	NPD6684	Approved
0.7558	Intermediate Similarity	NPD7146	Approved
0.7558	Intermediate Similarity	NPD4693	Phase 3
0.7558	Intermediate Similarity	NPD4694	Approved
0.7558	Intermediate Similarity	NPD7334	Approved
0.7558	Intermediate Similarity	NPD5279	Phase 3
0.7558	Intermediate Similarity	NPD5205	Approved
0.7558	Intermediate Similarity	NPD5330	Approved
0.7556	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.7473	Intermediate Similarity	NPD5695	Phase 3
0.7442	Intermediate Similarity	NPD1694	Approved
0.7436	Intermediate Similarity	NPD4691	Approved
0.7391	Intermediate Similarity	NPD7614	Phase 1
0.7386	Intermediate Similarity	NPD6903	Approved
0.7386	Intermediate Similarity	NPD5208	Approved
0.7386	Intermediate Similarity	NPD5737	Approved
0.7386	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD7331	Phase 2
0.7349	Intermediate Similarity	NPD4195	Approved
0.734	Intermediate Similarity	NPD6404	Discontinued
0.7333	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD5693	Phase 1
0.7326	Intermediate Similarity	NPD4786	Approved
0.7312	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD6084	Phase 2
0.7312	Intermediate Similarity	NPD7902	Approved
0.7308	Intermediate Similarity	NPD4137	Phase 3
0.7303	Intermediate Similarity	NPD5328	Approved
0.7303	Intermediate Similarity	NPD6673	Approved
0.7303	Intermediate Similarity	NPD6080	Approved
0.7303	Intermediate Similarity	NPD4753	Phase 2
0.7303	Intermediate Similarity	NPD6904	Approved
0.7253	Intermediate Similarity	NPD6399	Phase 3
0.7237	Intermediate Similarity	NPD7341	Phase 2
0.7234	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD5692	Phase 3
0.7222	Intermediate Similarity	NPD5207	Approved
0.7222	Intermediate Similarity	NPD4096	Approved
0.7215	Intermediate Similarity	NPD4747	Approved
0.716	Intermediate Similarity	NPD4058	Approved
0.7159	Intermediate Similarity	NPD6098	Approved
0.7143	Intermediate Similarity	NPD6050	Approved
0.7143	Intermediate Similarity	NPD5694	Approved
0.7125	Intermediate Similarity	NPD5276	Approved
0.7097	Intermediate Similarity	NPD4629	Approved
0.7097	Intermediate Similarity	NPD5210	Approved
0.7065	Intermediate Similarity	NPD4202	Approved
0.7024	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5221	Approved
0.7021	Intermediate Similarity	NPD5222	Approved
0.7021	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD4518	Approved
0.6989	Remote Similarity	NPD6001	Approved
0.6989	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7900	Approved
0.6977	Remote Similarity	NPD4692	Approved
0.6977	Remote Similarity	NPD4139	Approved
0.6951	Remote Similarity	NPD4687	Approved
0.6951	Remote Similarity	NPD5733	Approved
0.6947	Remote Similarity	NPD5173	Approved
0.6932	Remote Similarity	NPD3668	Phase 3
0.6915	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4756	Discovery
0.69	Remote Similarity	NPD5697	Approved
0.6892	Remote Similarity	NPD287	Approved
0.6882	Remote Similarity	NPD5133	Approved
0.6875	Remote Similarity	NPD4225	Approved
0.6869	Remote Similarity	NPD5141	Approved
0.6854	Remote Similarity	NPD5363	Approved
0.6854	Remote Similarity	NPD1696	Phase 3
0.6848	Remote Similarity	NPD5785	Approved
0.6842	Remote Similarity	NPD4194	Approved
0.6842	Remote Similarity	NPD4191	Approved
0.6842	Remote Similarity	NPD4193	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD7732	Phase 3
0.6842	Remote Similarity	NPD4192	Approved
0.6832	Remote Similarity	NPD6881	Approved
0.6832	Remote Similarity	NPD6899	Approved
0.6832	Remote Similarity	NPD6011	Approved
0.6818	Remote Similarity	NPD4788	Approved
0.6804	Remote Similarity	NPD5286	Approved
0.6804	Remote Similarity	NPD4696	Approved
0.6804	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD5285	Approved
0.6804	Remote Similarity	NPD7639	Approved
0.68	Remote Similarity	NPD6402	Approved
0.68	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6675	Approved
0.6774	Remote Similarity	NPD6411	Approved
0.6771	Remote Similarity	NPD4755	Approved
0.6765	Remote Similarity	NPD6013	Approved
0.6765	Remote Similarity	NPD6014	Approved
0.6765	Remote Similarity	NPD6012	Approved
0.6753	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5654	Approved
0.6735	Remote Similarity	NPD5223	Approved
0.6733	Remote Similarity	NPD5701	Approved
0.6709	Remote Similarity	NPD4224	Phase 2
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6701	Remote Similarity	NPD7638	Approved
0.6699	Remote Similarity	NPD6883	Approved
0.6699	Remote Similarity	NPD7290	Approved
0.6699	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD5091	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6635	Remote Similarity	NPD6650	Approved
0.6635	Remote Similarity	NPD8130	Phase 1
0.6635	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD6869	Approved
0.6635	Remote Similarity	NPD6649	Approved
0.6635	Remote Similarity	NPD6847	Approved
0.6633	Remote Similarity	NPD4700	Approved
0.6632	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6372	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.66	Remote Similarity	NPD5174	Approved
0.66	Remote Similarity	NPD5175	Approved
0.6598	Remote Similarity	NPD5959	Approved
0.6591	Remote Similarity	NPD857	Phase 3
0.6571	Remote Similarity	NPD8297	Approved
0.6571	Remote Similarity	NPD6882	Approved
0.6559	Remote Similarity	NPD6101	Approved
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4269	Approved
0.6517	Remote Similarity	NPD4270	Approved
0.6509	Remote Similarity	NPD4632	Approved
0.6506	Remote Similarity	NPD4243	Approved
0.6477	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5362	Discontinued
0.6444	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3172	Approved
0.6436	Remote Similarity	NPD4754	Approved
0.6436	Remote Similarity	NPD6052	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.6408	Remote Similarity	NPD6614	Approved
0.6404	Remote Similarity	NPD8028	Phase 2
0.6395	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6868	Approved
0.6389	Remote Similarity	NPD6274	Approved
0.6353	Remote Similarity	NPD4785	Approved
0.6353	Remote Similarity	NPD4784	Approved
0.6351	Remote Similarity	NPD3194	Approved
0.6351	Remote Similarity	NPD3196	Approved
0.6351	Remote Similarity	NPD4266	Approved
0.6351	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD3195	Phase 2
0.6346	Remote Similarity	NPD5168	Approved
0.6346	Remote Similarity	NPD4729	Approved
0.6346	Remote Similarity	NPD4730	Approved
0.6346	Remote Similarity	NPD5128	Approved
0.633	Remote Similarity	NPD6317	Approved
0.633	Remote Similarity	NPD6009	Approved
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD6008	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.631	Remote Similarity	NPD6081	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