NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	2.149
LogD:	2.345
LogS:	-3.37
# Rotatable Bonds:	0
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	5.071
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.603
MDCK Permeability:	1.4713226846652105e-05
Pgp-inhibitor:	0.8
Pgp-substrate:	0.07
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882
Plasma Protein Binding (PPB):	66.62137603759766%
Volume Distribution (VD):	2.92
Pgp-substrate:	42.319515228271484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.798

ADMET: Excretion

Clearance (CL):	13.187
Half-life (T1/2):	0.607

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.554
Carcinogencity:	0.922
Eye Corrosion:	0.13
Eye Irritation:	0.47
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC297398

Natural Product ID:	NPC297398
*Common Name:**	(+)-(5R,7S,9R,10S)-7-Hydroxy-7,12-Epidioxycadinan-3,6(11)-Dien-2-One
IUPAC Name:	(4aS,6R,6aS,10aR)-4a-hydroxy-1,6,9-trimethyl-2,5,6,6a,7,10a-hexahydrobenzo[f][1,2]benzodioxin-8-one
Synonyms:
Standard InCHIKey:	IGIQZZAVYBCVDN-ZFVXVEAMSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-4-12-11(5-13(8)16)9(2)6-15(17)14(12)10(3)7-18-19-15/h4,9,11-12,17H,5-7H2,1-3H3/t9-,11+,12+,15+/m1/s1
SMILES:	C[C@@H]1C[C@]2(O)OOCC(=C2[C@@H]2[C@H]1CC(=O)C(=C2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477570
PubChem CID:	25016669
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[15679321]
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679321]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[18620454]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26814	Consolida pubescens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8654	Digitalis viridiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26814	Consolida pubescens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26592	Isaria cretacea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13073	Thymus bashkiriensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9281	Melampodium diffusum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13720	Deparia lancea	Species	Athyriaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[556184]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	5000.0	nM	PMID[556184]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[556184]

☑ 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 NPC297398 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	171
0.1-0.2	1041
0.2-0.3	4325
0.3-0.4	10717
0.4-0.5	14079
0.5-0.6	7363
0.6-0.7	3957
0.7-0.8	975
0.8-0.85	64
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8846	High Similarity	NPC472305
0.8642	High Similarity	NPC472301
0.8519	High Similarity	NPC308038
0.85	High Similarity	NPC266193
0.85	High Similarity	NPC34110
0.85	High Similarity	NPC257666
0.8488	Intermediate Similarity	NPC48107
0.8434	Intermediate Similarity	NPC93590
0.8415	Intermediate Similarity	NPC271104
0.8409	Intermediate Similarity	NPC473998
0.8395	Intermediate Similarity	NPC253561
0.8395	Intermediate Similarity	NPC62336
0.8395	Intermediate Similarity	NPC80088
0.8391	Intermediate Similarity	NPC472983
0.8375	Intermediate Similarity	NPC7629
0.8375	Intermediate Similarity	NPC263582
0.8375	Intermediate Similarity	NPC76966
0.8375	Intermediate Similarity	NPC186554
0.8375	Intermediate Similarity	NPC151622
0.8333	Intermediate Similarity	NPC49019
0.8313	Intermediate Similarity	NPC226068
0.8293	Intermediate Similarity	NPC170394
0.8272	Intermediate Similarity	NPC97377
0.8256	Intermediate Similarity	NPC472985
0.8256	Intermediate Similarity	NPC472986
0.8256	Intermediate Similarity	NPC472974
0.8235	Intermediate Similarity	NPC476412
0.8228	Intermediate Similarity	NPC35656
0.8222	Intermediate Similarity	NPC8993
0.8202	Intermediate Similarity	NPC472978
0.8193	Intermediate Similarity	NPC476809
0.8193	Intermediate Similarity	NPC172013
0.8182	Intermediate Similarity	NPC309603
0.8182	Intermediate Similarity	NPC472973
0.8182	Intermediate Similarity	NPC473999
0.8182	Intermediate Similarity	NPC36668
0.8182	Intermediate Similarity	NPC118011
0.8171	Intermediate Similarity	NPC207772
0.8152	Intermediate Similarity	NPC170131
0.814	Intermediate Similarity	NPC476426
0.8111	Intermediate Similarity	NPC109305
0.8095	Intermediate Similarity	NPC119229
0.8095	Intermediate Similarity	NPC116797
0.8095	Intermediate Similarity	NPC278459
0.809	Intermediate Similarity	NPC128672
0.809	Intermediate Similarity	NPC134321
0.8072	Intermediate Similarity	NPC281138
0.8068	Intermediate Similarity	NPC104560
0.8068	Intermediate Similarity	NPC72397
0.8065	Intermediate Similarity	NPC478056
0.8049	Intermediate Similarity	NPC74995
0.8049	Intermediate Similarity	NPC203403
0.8049	Intermediate Similarity	NPC197659
0.8046	Intermediate Similarity	NPC473226
0.8046	Intermediate Similarity	NPC194417
0.8043	Intermediate Similarity	NPC117133
0.8025	Intermediate Similarity	NPC476795
0.8023	Intermediate Similarity	NPC30486
0.8022	Intermediate Similarity	NPC472977
0.8022	Intermediate Similarity	NPC472976
0.8	Intermediate Similarity	NPC116726
0.8	Intermediate Similarity	NPC247586
0.8	Intermediate Similarity	NPC103486
0.8	Intermediate Similarity	NPC475806
0.7978	Intermediate Similarity	NPC5509
0.7976	Intermediate Similarity	NPC104120
0.7976	Intermediate Similarity	NPC157895
0.7976	Intermediate Similarity	NPC471514
0.7976	Intermediate Similarity	NPC2482
0.7976	Intermediate Similarity	NPC148685
0.7957	Intermediate Similarity	NPC253826
0.7955	Intermediate Similarity	NPC476409
0.7955	Intermediate Similarity	NPC181327
0.7952	Intermediate Similarity	NPC475994
0.7952	Intermediate Similarity	NPC471409
0.7952	Intermediate Similarity	NPC198240
0.7952	Intermediate Similarity	NPC275494
0.7952	Intermediate Similarity	NPC74410
0.7935	Intermediate Similarity	NPC476245
0.7927	Intermediate Similarity	NPC470525
0.7927	Intermediate Similarity	NPC180886
0.7912	Intermediate Similarity	NPC476416
0.7912	Intermediate Similarity	NPC69454
0.7907	Intermediate Similarity	NPC64600
0.7907	Intermediate Similarity	NPC97913
0.7907	Intermediate Similarity	NPC105173
0.7889	Intermediate Similarity	NPC473099
0.7889	Intermediate Similarity	NPC48010
0.7889	Intermediate Similarity	NPC230332
0.7882	Intermediate Similarity	NPC90055
0.7882	Intermediate Similarity	NPC121984
0.7882	Intermediate Similarity	NPC473217
0.7882	Intermediate Similarity	NPC55869
0.7882	Intermediate Similarity	NPC6663
0.7865	Intermediate Similarity	NPC471791
0.7865	Intermediate Similarity	NPC473229
0.7865	Intermediate Similarity	NPC471793
0.7857	Intermediate Similarity	NPC152061
0.7849	Intermediate Similarity	NPC249954
0.7849	Intermediate Similarity	NPC250757
0.7849	Intermediate Similarity	NPC301534
0.7849	Intermediate Similarity	NPC472941
0.7849	Intermediate Similarity	NPC456
0.7841	Intermediate Similarity	NPC322159
0.7841	Intermediate Similarity	NPC198761
0.7841	Intermediate Similarity	NPC82979
0.7831	Intermediate Similarity	NPC165711
0.7831	Intermediate Similarity	NPC61952
0.7826	Intermediate Similarity	NPC299100
0.7826	Intermediate Similarity	NPC196227
0.7816	Intermediate Similarity	NPC472865
0.7816	Intermediate Similarity	NPC164577
0.7816	Intermediate Similarity	NPC248758
0.7816	Intermediate Similarity	NPC302360
0.7812	Intermediate Similarity	NPC293753
0.7802	Intermediate Similarity	NPC233455
0.7802	Intermediate Similarity	NPC145067
0.7802	Intermediate Similarity	NPC252433
0.7802	Intermediate Similarity	NPC4036
0.7802	Intermediate Similarity	NPC65120
0.7802	Intermediate Similarity	NPC233116
0.7802	Intermediate Similarity	NPC472975
0.7802	Intermediate Similarity	NPC158030
0.7802	Intermediate Similarity	NPC63748
0.7789	Intermediate Similarity	NPC474012
0.7789	Intermediate Similarity	NPC476299
0.7789	Intermediate Similarity	NPC476274
0.7778	Intermediate Similarity	NPC119416
0.7778	Intermediate Similarity	NPC473100
0.7778	Intermediate Similarity	NPC477973
0.7778	Intermediate Similarity	NPC281524
0.7778	Intermediate Similarity	NPC262043
0.7766	Intermediate Similarity	NPC320306
0.7765	Intermediate Similarity	NPC233352
0.7765	Intermediate Similarity	NPC469637
0.7765	Intermediate Similarity	NPC824
0.7765	Intermediate Similarity	NPC108955
0.7765	Intermediate Similarity	NPC45495
0.7765	Intermediate Similarity	NPC306095
0.7765	Intermediate Similarity	NPC472478
0.7765	Intermediate Similarity	NPC138492
0.7753	Intermediate Similarity	NPC136948
0.7753	Intermediate Similarity	NPC471792
0.7742	Intermediate Similarity	NPC180950
0.7742	Intermediate Similarity	NPC476174
0.7742	Intermediate Similarity	NPC271195
0.7742	Intermediate Similarity	NPC259286
0.7742	Intermediate Similarity	NPC183012
0.7738	Intermediate Similarity	NPC297996
0.7738	Intermediate Similarity	NPC178852
0.7738	Intermediate Similarity	NPC189485
0.7732	Intermediate Similarity	NPC478057
0.7732	Intermediate Similarity	NPC95899
0.7727	Intermediate Similarity	NPC474680
0.7727	Intermediate Similarity	NPC132228
0.7727	Intermediate Similarity	NPC241512
0.7727	Intermediate Similarity	NPC189311
0.7727	Intermediate Similarity	NPC6185
0.7727	Intermediate Similarity	NPC8518
0.7727	Intermediate Similarity	NPC471224
0.7727	Intermediate Similarity	NPC470574
0.7727	Intermediate Similarity	NPC274724
0.7727	Intermediate Similarity	NPC474083
0.7727	Intermediate Similarity	NPC70685
0.7727	Intermediate Similarity	NPC263997
0.7717	Intermediate Similarity	NPC295643
0.7717	Intermediate Similarity	NPC474736
0.7717	Intermediate Similarity	NPC151722
0.7717	Intermediate Similarity	NPC272075
0.7717	Intermediate Similarity	NPC214756
0.7717	Intermediate Similarity	NPC472930
0.7717	Intermediate Similarity	NPC472303
0.7708	Intermediate Similarity	NPC476223
0.7708	Intermediate Similarity	NPC476240
0.7708	Intermediate Similarity	NPC81530
0.7708	Intermediate Similarity	NPC224720
0.7708	Intermediate Similarity	NPC472637
0.7701	Intermediate Similarity	NPC66764
0.7701	Intermediate Similarity	NPC110150
0.7701	Intermediate Similarity	NPC251475
0.7701	Intermediate Similarity	NPC57370
0.7701	Intermediate Similarity	NPC169941
0.7701	Intermediate Similarity	NPC105803
0.7692	Intermediate Similarity	NPC476437
0.7692	Intermediate Similarity	NPC476369
0.7692	Intermediate Similarity	NPC85173
0.7692	Intermediate Similarity	NPC191684
0.7692	Intermediate Similarity	NPC474209
0.7692	Intermediate Similarity	NPC475823
0.7684	Intermediate Similarity	NPC166745
0.7684	Intermediate Similarity	NPC197386
0.7684	Intermediate Similarity	NPC103051
0.7684	Intermediate Similarity	NPC235464
0.7674	Intermediate Similarity	NPC473420
0.7674	Intermediate Similarity	NPC471898
0.7667	Intermediate Similarity	NPC206060
0.7667	Intermediate Similarity	NPC7280
0.7667	Intermediate Similarity	NPC472802
0.7667	Intermediate Similarity	NPC193843
0.7667	Intermediate Similarity	NPC472870

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 NPC297398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1422
0.2-0.3	3701
0.3-0.4	2569
0.4-0.5	860
0.5-0.6	244
0.6-0.7	178
0.7-0.8	19
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
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7802	Intermediate Similarity	NPD7515	Phase 2
0.7765	Intermediate Similarity	NPD4695	Discontinued
0.764	Intermediate Similarity	NPD4623	Approved
0.764	Intermediate Similarity	NPD4519	Discontinued
0.7634	Intermediate Similarity	NPD7748	Approved
0.7614	Intermediate Similarity	NPD3133	Approved
0.7614	Intermediate Similarity	NPD3666	Approved
0.7614	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD6079	Approved
0.7586	Intermediate Similarity	NPD3667	Approved
0.7582	Intermediate Similarity	NPD5328	Approved
0.7474	Intermediate Similarity	NPD5221	Approved
0.7474	Intermediate Similarity	NPD5222	Approved
0.7474	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5211	Phase 2
0.7444	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4786	Approved
0.7396	Intermediate Similarity	NPD7902	Approved
0.7396	Intermediate Similarity	NPD5173	Approved
0.7391	Intermediate Similarity	NPD4753	Phase 2
0.7386	Intermediate Similarity	NPD4221	Approved
0.7386	Intermediate Similarity	NPD4223	Phase 3
0.734	Intermediate Similarity	NPD4202	Approved
0.73	Intermediate Similarity	NPD5141	Approved
0.7292	Intermediate Similarity	NPD4697	Phase 3
0.7253	Intermediate Similarity	NPD5690	Phase 2
0.7253	Intermediate Similarity	NPD5279	Phase 3
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7222	Intermediate Similarity	NPD4197	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD4755	Approved
0.7191	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5210	Approved
0.7188	Intermediate Similarity	NPD5695	Phase 3
0.7188	Intermediate Similarity	NPD4629	Approved
0.7174	Intermediate Similarity	NPD3573	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7158	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD5329	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD1696	Phase 3
0.7126	Intermediate Similarity	NPD3617	Approved
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.7097	Intermediate Similarity	NPD6672	Approved
0.7097	Intermediate Similarity	NPD5737	Approved
0.7083	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7900	Approved
0.7071	Intermediate Similarity	NPD4700	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7065	Intermediate Similarity	NPD5280	Approved
0.7065	Intermediate Similarity	NPD6684	Approved
0.7065	Intermediate Similarity	NPD4693	Phase 3
0.7065	Intermediate Similarity	NPD4690	Approved
0.7065	Intermediate Similarity	NPD7521	Approved
0.7065	Intermediate Similarity	NPD4694	Approved
0.7065	Intermediate Similarity	NPD7334	Approved
0.7065	Intermediate Similarity	NPD6409	Approved
0.7065	Intermediate Similarity	NPD5205	Approved
0.7065	Intermediate Similarity	NPD4138	Approved
0.7065	Intermediate Similarity	NPD5330	Approved
0.7065	Intermediate Similarity	NPD4689	Approved
0.7065	Intermediate Similarity	NPD4688	Approved
0.7065	Intermediate Similarity	NPD7146	Approved
0.7053	Intermediate Similarity	NPD5284	Approved
0.7053	Intermediate Similarity	NPD5281	Approved
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.7037	Intermediate Similarity	NPD7115	Discovery
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.7021	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5697	Approved
0.697	Remote Similarity	NPD5696	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6923	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6915	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6903	Approved
0.6905	Remote Similarity	NPD4691	Approved
0.6893	Remote Similarity	NPD5739	Approved
0.6893	Remote Similarity	NPD7128	Approved
0.6893	Remote Similarity	NPD6675	Approved
0.6893	Remote Similarity	NPD6402	Approved
0.6863	Remote Similarity	NPD4754	Approved
0.6857	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD6014	Approved
0.6857	Remote Similarity	NPD6012	Approved
0.6854	Remote Similarity	NPD4195	Approved
0.6829	Remote Similarity	NPD7331	Phase 2
0.6827	Remote Similarity	NPD5701	Approved
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.68	Remote Similarity	NPD4225	Approved
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6792	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD4137	Phase 3
0.6774	Remote Similarity	NPD5363	Approved
0.6768	Remote Similarity	NPD7614	Phase 1
0.6762	Remote Similarity	NPD7320	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD5168	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD5128	Approved
0.6739	Remote Similarity	NPD4788	Approved
0.6733	Remote Similarity	NPD6404	Discontinued
0.6731	Remote Similarity	NPD4767	Approved
0.6731	Remote Similarity	NPD4768	Approved
0.6729	Remote Similarity	NPD8130	Phase 1
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD6649	Approved
0.6729	Remote Similarity	NPD6650	Approved
0.6707	Remote Similarity	NPD7341	Phase 2
0.6706	Remote Similarity	NPD4747	Approved
0.6701	Remote Similarity	NPD5693	Phase 1
0.6698	Remote Similarity	NPD6373	Approved
0.6698	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4756	Discovery
0.6606	Remote Similarity	NPD4632	Approved
0.6598	Remote Similarity	NPD4096	Approved
0.6598	Remote Similarity	NPD5692	Phase 3
0.6596	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5215	Approved
0.6574	Remote Similarity	NPD5217	Approved
0.6574	Remote Similarity	NPD5216	Approved
0.6574	Remote Similarity	NPD5127	Approved
0.6562	Remote Similarity	NPD5208	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6411	Approved
0.6531	Remote Similarity	NPD6050	Approved
0.6531	Remote Similarity	NPD5694	Approved
0.6522	Remote Similarity	NPD4692	Approved
0.6522	Remote Similarity	NPD4139	Approved
0.6517	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6412	Phase 2
0.6486	Remote Similarity	NPD6274	Approved
0.6486	Remote Similarity	NPD6868	Approved
0.6484	Remote Similarity	NPD7645	Phase 2
0.6477	Remote Similarity	NPD5733	Approved
0.6477	Remote Similarity	NPD4687	Approved
0.6465	Remote Similarity	NPD5133	Approved
0.6463	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4270	Approved
0.6449	Remote Similarity	NPD6686	Approved
0.6442	Remote Similarity	NPD5091	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6437	Remote Similarity	NPD5276	Approved
0.6436	Remote Similarity	NPD7732	Phase 3
0.6429	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD6317	Approved
0.6429	Remote Similarity	NPD5785	Approved
0.6429	Remote Similarity	NPD6009	Approved
0.6415	Remote Similarity	NPD6008	Approved
0.6413	Remote Similarity	NPD7525	Registered
0.641	Remote Similarity	NPD342	Phase 1
0.6404	Remote Similarity	NPD8264	Approved
0.6404	Remote Similarity	NPD7339	Approved
0.6404	Remote Similarity	NPD6942	Approved
0.64	Remote Similarity	NPD6001	Approved
0.6396	Remote Similarity	NPD5167	Approved
0.6392	Remote Similarity	NPD4518	Approved
0.6389	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5362	Discontinued
0.6372	Remote Similarity	NPD6335	Approved
0.6372	Remote Similarity	NPD6313	Approved
0.6372	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6053	Discontinued

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