NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	1.302
LogD:	0.498
LogS:	-1.358
# Rotatable Bonds:	3
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	4.521
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:	-4.483
MDCK Permeability:	5.1565693865995854e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.371
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.885
Plasma Protein Binding (PPB):	48.036033630371094%
Volume Distribution (VD):	0.642
Pgp-substrate:	66.37906646728516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.392
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	7.124
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.396
AMES Toxicity:	0.664
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.928
Carcinogencity:	0.822
Eye Corrosion:	0.962
Eye Irritation:	0.967
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC45495

Natural Product ID:	NPC45495
*Common Name:**	12-Hydroxychiloscypha-2,7-Dione
IUPAC Name:	(1S,7S,7aS)-1-[2-(hydroxymethyl)prop-2-enoyl]-7,7a-dimethyl-2,3,6,7-tetrahydro-1H-inden-5-one
Synonyms:
Standard InCHIKey:	HSEYGUUBMYCCIJ-PSOPSSQASA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9(8-16)14(18)13-5-4-11-7-12(17)6-10(2)15(11,13)3/h7,10,13,16H,1,4-6,8H2,2-3H3/t10-,13+,15+/m0/s1
SMILES:	C=C(CO)C(=O)[C@H]1CCC2=CC(=O)C[C@H](C)[C@@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462819
PubChem CID:	10586644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO8475	Chiloscyphus rivularis	Species	Lophocoleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9463110]
NPO8475	Chiloscyphus rivularis	Species	Lophocoleaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	500.0	ug ml-1	PMID[487819]

☑ 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 NPC45495 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	143
0.1-0.2	1112
0.2-0.3	5838
0.3-0.4	14634
0.4-0.5	9920
0.5-0.6	6498
0.6-0.7	3663
0.7-0.8	844
0.8-0.85	36
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC7232
0.8961	High Similarity	NPC62336
0.8947	High Similarity	NPC263582
0.878	High Similarity	NPC194417
0.8718	High Similarity	NPC475994
0.8701	High Similarity	NPC470525
0.8659	High Similarity	NPC474853
0.8659	High Similarity	NPC179006
0.8625	High Similarity	NPC136150
0.8608	High Similarity	NPC308038
0.8571	High Similarity	NPC114236
0.85	High Similarity	NPC157895
0.85	High Similarity	NPC148685
0.85	High Similarity	NPC104120
0.8471	Intermediate Similarity	NPC123912
0.8462	Intermediate Similarity	NPC469646
0.8415	Intermediate Similarity	NPC62214
0.8395	Intermediate Similarity	NPC116797
0.8354	Intermediate Similarity	NPC97377
0.8354	Intermediate Similarity	NPC74995
0.8353	Intermediate Similarity	NPC474854
0.8313	Intermediate Similarity	NPC85774
0.8313	Intermediate Similarity	NPC214043
0.8313	Intermediate Similarity	NPC473246
0.8313	Intermediate Similarity	NPC329043
0.8313	Intermediate Similarity	NPC237712
0.8313	Intermediate Similarity	NPC161423
0.8313	Intermediate Similarity	NPC58841
0.8313	Intermediate Similarity	NPC227064
0.8313	Intermediate Similarity	NPC476412
0.8313	Intermediate Similarity	NPC230527
0.8313	Intermediate Similarity	NPC7927
0.8313	Intermediate Similarity	NPC321187
0.8312	Intermediate Similarity	NPC186042
0.8293	Intermediate Similarity	NPC93590
0.8272	Intermediate Similarity	NPC172013
0.8272	Intermediate Similarity	NPC472478
0.8256	Intermediate Similarity	NPC472475
0.8256	Intermediate Similarity	NPC309603
0.8256	Intermediate Similarity	NPC473999
0.8256	Intermediate Similarity	NPC472477
0.8235	Intermediate Similarity	NPC287079
0.8235	Intermediate Similarity	NPC93778
0.8214	Intermediate Similarity	NPC469948
0.8214	Intermediate Similarity	NPC471224
0.8214	Intermediate Similarity	NPC474083
0.8214	Intermediate Similarity	NPC470574
0.8205	Intermediate Similarity	NPC215050
0.8193	Intermediate Similarity	NPC474748
0.8182	Intermediate Similarity	NPC474736
0.8182	Intermediate Similarity	NPC474807
0.8182	Intermediate Similarity	NPC109305
0.8161	Intermediate Similarity	NPC48010
0.8161	Intermediate Similarity	NPC230332
0.8148	Intermediate Similarity	NPC229204
0.8148	Intermediate Similarity	NPC472490
0.8148	Intermediate Similarity	NPC19900
0.8148	Intermediate Similarity	NPC152061
0.814	Intermediate Similarity	NPC471724
0.8125	Intermediate Similarity	NPC266193
0.8125	Intermediate Similarity	NPC197659
0.8125	Intermediate Similarity	NPC257666
0.8118	Intermediate Similarity	NPC474733
0.8118	Intermediate Similarity	NPC145879
0.8118	Intermediate Similarity	NPC474778
0.8118	Intermediate Similarity	NPC474732
0.8118	Intermediate Similarity	NPC472974
0.8118	Intermediate Similarity	NPC476043
0.8118	Intermediate Similarity	NPC31564
0.8118	Intermediate Similarity	NPC327115
0.8118	Intermediate Similarity	NPC469994
0.8111	Intermediate Similarity	NPC29152
0.8101	Intermediate Similarity	NPC474011
0.8095	Intermediate Similarity	NPC165064
0.8077	Intermediate Similarity	NPC275098
0.8072	Intermediate Similarity	NPC103486
0.8072	Intermediate Similarity	NPC151519
0.8072	Intermediate Similarity	NPC38796
0.8072	Intermediate Similarity	NPC158411
0.8068	Intermediate Similarity	NPC475806
0.8068	Intermediate Similarity	NPC473998
0.8049	Intermediate Similarity	NPC233352
0.8049	Intermediate Similarity	NPC2482
0.8049	Intermediate Similarity	NPC824
0.8049	Intermediate Similarity	NPC138492
0.8049	Intermediate Similarity	NPC271104
0.8046	Intermediate Similarity	NPC472970
0.8046	Intermediate Similarity	NPC472971
0.8046	Intermediate Similarity	NPC170775
0.8046	Intermediate Similarity	NPC472489
0.8046	Intermediate Similarity	NPC214387
0.8025	Intermediate Similarity	NPC275494
0.8025	Intermediate Similarity	NPC471409
0.8025	Intermediate Similarity	NPC178852
0.8025	Intermediate Similarity	NPC297996
0.8023	Intermediate Similarity	NPC475740
0.8023	Intermediate Similarity	NPC136548
0.8023	Intermediate Similarity	NPC96496
0.8023	Intermediate Similarity	NPC58063
0.8022	Intermediate Similarity	NPC156546
0.8	Intermediate Similarity	NPC476426
0.8	Intermediate Similarity	NPC36350
0.8	Intermediate Similarity	NPC70685
0.8	Intermediate Similarity	NPC215481
0.7978	Intermediate Similarity	NPC115021
0.7978	Intermediate Similarity	NPC472930
0.7978	Intermediate Similarity	NPC69454
0.7976	Intermediate Similarity	NPC470165
0.7976	Intermediate Similarity	NPC97913
0.7973	Intermediate Similarity	NPC212210
0.7957	Intermediate Similarity	NPC472924
0.7955	Intermediate Similarity	NPC191684
0.7955	Intermediate Similarity	NPC477147
0.7955	Intermediate Similarity	NPC51486
0.7955	Intermediate Similarity	NPC472476
0.7955	Intermediate Similarity	NPC477149
0.7952	Intermediate Similarity	NPC477372
0.7952	Intermediate Similarity	NPC121984
0.7952	Intermediate Similarity	NPC14151
0.7931	Intermediate Similarity	NPC471793
0.7931	Intermediate Similarity	NPC193843
0.7931	Intermediate Similarity	NPC471722
0.7931	Intermediate Similarity	NPC328539
0.7931	Intermediate Similarity	NPC471791
0.7931	Intermediate Similarity	NPC249889
0.7931	Intermediate Similarity	NPC328313
0.7927	Intermediate Similarity	NPC281138
0.7927	Intermediate Similarity	NPC261125
0.7927	Intermediate Similarity	NPC181195
0.7912	Intermediate Similarity	NPC472941
0.7912	Intermediate Similarity	NPC456
0.7907	Intermediate Similarity	NPC118648
0.7907	Intermediate Similarity	NPC222613
0.7907	Intermediate Similarity	NPC472479
0.7907	Intermediate Similarity	NPC475022
0.7907	Intermediate Similarity	NPC472985
0.7907	Intermediate Similarity	NPC472986
0.7907	Intermediate Similarity	NPC198761
0.7907	Intermediate Similarity	NPC470955
0.7907	Intermediate Similarity	NPC72133
0.7901	Intermediate Similarity	NPC203403
0.7889	Intermediate Similarity	NPC8993
0.7889	Intermediate Similarity	NPC299100
0.7889	Intermediate Similarity	NPC53685
0.7882	Intermediate Similarity	NPC221758
0.7882	Intermediate Similarity	NPC59453
0.7882	Intermediate Similarity	NPC82902
0.7882	Intermediate Similarity	NPC472265
0.7882	Intermediate Similarity	NPC164577
0.7875	Intermediate Similarity	NPC77501
0.7875	Intermediate Similarity	NPC476795
0.7865	Intermediate Similarity	NPC272746
0.7865	Intermediate Similarity	NPC472814
0.7865	Intermediate Similarity	NPC233116
0.7865	Intermediate Similarity	NPC63748
0.7865	Intermediate Similarity	NPC177037
0.7857	Intermediate Similarity	NPC129080
0.7857	Intermediate Similarity	NPC20262
0.7857	Intermediate Similarity	NPC256750
0.7857	Intermediate Similarity	NPC477269
0.7857	Intermediate Similarity	NPC477271
0.7857	Intermediate Similarity	NPC477270
0.7857	Intermediate Similarity	NPC193347
0.7848	Intermediate Similarity	NPC247586
0.7841	Intermediate Similarity	NPC5509
0.7841	Intermediate Similarity	NPC268406
0.7841	Intermediate Similarity	NPC472973
0.7841	Intermediate Similarity	NPC326627
0.7841	Intermediate Similarity	NPC119416
0.7841	Intermediate Similarity	NPC472983
0.7841	Intermediate Similarity	NPC2983
0.7841	Intermediate Similarity	NPC1015
0.7841	Intermediate Similarity	NPC262043
0.7841	Intermediate Similarity	NPC86319
0.7841	Intermediate Similarity	NPC31985
0.7841	Intermediate Similarity	NPC186688
0.7841	Intermediate Similarity	NPC477943
0.7841	Intermediate Similarity	NPC275740
0.7841	Intermediate Similarity	NPC26959
0.7841	Intermediate Similarity	NPC310010
0.7841	Intermediate Similarity	NPC310236
0.7831	Intermediate Similarity	NPC471514
0.7831	Intermediate Similarity	NPC306095
0.7831	Intermediate Similarity	NPC472301
0.7826	Intermediate Similarity	NPC253826
0.7816	Intermediate Similarity	NPC312561
0.7816	Intermediate Similarity	NPC141292
0.7816	Intermediate Similarity	NPC317590
0.7816	Intermediate Similarity	NPC472484
0.7816	Intermediate Similarity	NPC472481
0.7816	Intermediate Similarity	NPC472482
0.7816	Intermediate Similarity	NPC136948
0.7805	Intermediate Similarity	NPC74410
0.7805	Intermediate Similarity	NPC207772
0.7802	Intermediate Similarity	NPC472932
0.7802	Intermediate Similarity	NPC476174
0.7802	Intermediate Similarity	NPC259286
0.7802	Intermediate Similarity	NPC271195
0.7802	Intermediate Similarity	NPC180950
0.7792	Intermediate Similarity	NPC117804

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 NPC45495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1704
0.2-0.3	4073
0.3-0.4	2255
0.4-0.5	549
0.5-0.6	204
0.6-0.7	189
0.7-0.8	33
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
0.8313	Intermediate Similarity	NPD3665	Phase 1
0.8313	Intermediate Similarity	NPD3133	Approved
0.8313	Intermediate Similarity	NPD3666	Approved
0.8118	Intermediate Similarity	NPD5279	Phase 3
0.8118	Intermediate Similarity	NPD3618	Phase 1
0.8072	Intermediate Similarity	NPD3667	Approved
0.7907	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4786	Approved
0.7865	Intermediate Similarity	NPD6079	Approved
0.7857	Intermediate Similarity	NPD4223	Phase 3
0.7857	Intermediate Similarity	NPD4221	Approved
0.7841	Intermediate Similarity	NPD5328	Approved
0.7841	Intermediate Similarity	NPD4753	Phase 2
0.7701	Intermediate Similarity	NPD5690	Phase 2
0.7674	Intermediate Similarity	NPD4197	Approved
0.7619	Intermediate Similarity	NPD4695	Discontinued
0.7609	Intermediate Similarity	NPD4629	Approved
0.7609	Intermediate Similarity	NPD5210	Approved
0.759	Intermediate Similarity	NPD3617	Approved
0.7586	Intermediate Similarity	NPD5329	Approved
0.7586	Intermediate Similarity	NPD5363	Approved
0.7582	Intermediate Similarity	NPD4202	Approved
0.7556	Intermediate Similarity	NPD5785	Approved
0.7527	Intermediate Similarity	NPD5221	Approved
0.7527	Intermediate Similarity	NPD5222	Approved
0.7527	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.7447	Intermediate Similarity	NPD5173	Approved
0.7386	Intermediate Similarity	NPD1696	Phase 3
0.7381	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4691	Approved
0.7356	Intermediate Similarity	NPD4788	Approved
0.7347	Intermediate Similarity	NPD5141	Approved
0.734	Intermediate Similarity	NPD4697	Phase 3
0.7303	Intermediate Similarity	NPD5330	Approved
0.7303	Intermediate Similarity	NPD7521	Approved
0.7303	Intermediate Similarity	NPD7334	Approved
0.7303	Intermediate Similarity	NPD6409	Approved
0.7303	Intermediate Similarity	NPD6684	Approved
0.7303	Intermediate Similarity	NPD7146	Approved
0.7294	Intermediate Similarity	NPD4195	Approved
0.7292	Intermediate Similarity	NPD5285	Approved
0.7292	Intermediate Similarity	NPD4696	Approved
0.7292	Intermediate Similarity	NPD5286	Approved
0.7273	Intermediate Similarity	NPD3668	Phase 3
0.7263	Intermediate Similarity	NPD6083	Phase 2
0.7263	Intermediate Similarity	NPD4755	Approved
0.7263	Intermediate Similarity	NPD6084	Phase 2
0.725	Intermediate Similarity	NPD4137	Phase 3
0.7241	Intermediate Similarity	NPD4269	Approved
0.7241	Intermediate Similarity	NPD4270	Approved
0.7234	Intermediate Similarity	NPD5695	Phase 3
0.7216	Intermediate Similarity	NPD5223	Approved
0.7174	Intermediate Similarity	NPD4096	Approved
0.716	Intermediate Similarity	NPD4747	Approved
0.7143	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD5225	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD4518	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4633	Approved
0.7113	Intermediate Similarity	NPD4700	Approved
0.7108	Intermediate Similarity	NPD4058	Approved
0.7097	Intermediate Similarity	NPD7515	Phase 2
0.7097	Intermediate Similarity	NPD5281	Approved
0.7097	Intermediate Similarity	NPD5284	Approved
0.7089	Intermediate Similarity	NPD7331	Phase 2
0.7073	Intermediate Similarity	NPD5276	Approved
0.7071	Intermediate Similarity	NPD5174	Approved
0.7071	Intermediate Similarity	NPD5175	Approved
0.7053	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6399	Phase 3
0.7011	Intermediate Similarity	NPD4252	Approved
0.701	Intermediate Similarity	NPD5696	Approved
0.699	Remote Similarity	NPD4634	Approved
0.6962	Remote Similarity	NPD7341	Phase 2
0.6941	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5369	Approved
0.6932	Remote Similarity	NPD4692	Approved
0.6932	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD5786	Approved
0.6916	Remote Similarity	NPD7115	Discovery
0.6905	Remote Similarity	NPD5733	Approved
0.6905	Remote Similarity	NPD4687	Approved
0.69	Remote Similarity	NPD4754	Approved
0.6863	Remote Similarity	NPD5697	Approved
0.6842	Remote Similarity	NPD5133	Approved
0.6837	Remote Similarity	NPD4225	Approved
0.6824	Remote Similarity	NPD6942	Approved
0.6824	Remote Similarity	NPD7339	Approved
0.6813	Remote Similarity	NPD1694	Approved
0.6796	Remote Similarity	NPD6899	Approved
0.6796	Remote Similarity	NPD6881	Approved
0.6796	Remote Similarity	NPD6011	Approved
0.6796	Remote Similarity	NPD4730	Approved
0.6796	Remote Similarity	NPD4729	Approved
0.6796	Remote Similarity	NPD5128	Approved
0.6796	Remote Similarity	NPD5168	Approved
0.6778	Remote Similarity	NPD5362	Discontinued
0.6774	Remote Similarity	NPD5208	Approved
0.6771	Remote Similarity	NPD7748	Approved
0.6771	Remote Similarity	NPD5282	Discontinued
0.6768	Remote Similarity	NPD7640	Approved
0.6768	Remote Similarity	NPD7639	Approved
0.6768	Remote Similarity	NPD6404	Discontinued
0.6765	Remote Similarity	NPD6402	Approved
0.6765	Remote Similarity	NPD7128	Approved
0.6765	Remote Similarity	NPD4767	Approved
0.6765	Remote Similarity	NPD5739	Approved
0.6765	Remote Similarity	NPD6675	Approved
0.6765	Remote Similarity	NPD4768	Approved
0.675	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6411	Approved
0.6737	Remote Similarity	NPD5693	Phase 1
0.6731	Remote Similarity	NPD6013	Approved
0.6731	Remote Similarity	NPD6012	Approved
0.6731	Remote Similarity	NPD6014	Approved
0.6707	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6926	Approved
0.6706	Remote Similarity	NPD6924	Approved
0.6705	Remote Similarity	NPD6929	Approved
0.6702	Remote Similarity	NPD6080	Approved
0.6702	Remote Similarity	NPD6904	Approved
0.6702	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6412	Phase 2
0.6699	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD5091	Approved
0.6632	Remote Similarity	NPD5207	Approved
0.6632	Remote Similarity	NPD5692	Phase 3
0.663	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6931	Approved
0.6629	Remote Similarity	NPD5368	Approved
0.6629	Remote Similarity	NPD6930	Phase 2
0.6623	Remote Similarity	NPD287	Approved
0.6604	Remote Similarity	NPD6847	Approved
0.6604	Remote Similarity	NPD8130	Phase 1
0.6604	Remote Similarity	NPD6650	Approved
0.6604	Remote Similarity	NPD6617	Approved
0.6604	Remote Similarity	NPD5215	Approved
0.6604	Remote Similarity	NPD5127	Approved
0.6604	Remote Similarity	NPD5217	Approved
0.6604	Remote Similarity	NPD6869	Approved
0.6604	Remote Similarity	NPD5216	Approved
0.6604	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD6372	Approved
0.6566	Remote Similarity	NPD7902	Approved
0.6562	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD5694	Approved
0.6562	Remote Similarity	NPD6050	Approved
0.6559	Remote Similarity	NPD6098	Approved
0.6552	Remote Similarity	NPD6933	Approved
0.6542	Remote Similarity	NPD6882	Approved
0.6542	Remote Similarity	NPD8297	Approved
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5290	Discontinued
0.6489	Remote Similarity	NPD3573	Approved
0.6489	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4522	Approved
0.6484	Remote Similarity	NPD6435	Approved
0.6481	Remote Similarity	NPD4632	Approved
0.6477	Remote Similarity	NPD5776	Phase 2
0.6477	Remote Similarity	NPD6925	Approved
0.6471	Remote Similarity	NPD4243	Approved
0.6449	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD342	Phase 1

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