NPASS Compound

Structure

CID146388 OpenBabel06191715502D 29 32 0 0 1 0 0 0 0 0999 V2000 3.6340 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.1340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0981 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2321 -0.1340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2321 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9641 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 23 1 0 0 0 0 13 28 1 0 0 0 0 14 23 1 1 0 0 0 15 18 1 0 0 0 0 15 24 1 6 0 0 0 16 19 2 0 0 0 0 17 28 1 0 0 0 0 18 25 2 0 0 0 0 19 29 1 0 0 0 0 20 23 1 6 0 0 0 20 24 1 0 0 0 0 21 24 1 6 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 23 3 1 6 0 0 0 24 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.21
Volume:	417.567
LogP:	3.307
LogD:	3.253
LogS:	-4.355
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.784
Synthetic Accessibility Score:	4.315
Fsp3:	0.583
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:	-4.801
MDCK Permeability:	1.962369969987776e-05
Pgp-inhibitor:	0.904
Pgp-substrate:	0.785
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.257
Plasma Protein Binding (PPB):	96.7531967163086%
Volume Distribution (VD):	0.791
Pgp-substrate:	7.291728973388672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.704
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.529
CYP2C19-substrate:	0.689
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.793
CYP2D6-inhibitor:	0.183
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.74
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	11.691
Half-life (T1/2):	0.536

ADMET: Toxicity

hERG Blockers:	0.384
Human Hepatotoxicity (H-HT):	0.393
Drug-inuced Liver Injury (DILI):	0.396
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.111
Carcinogencity:	0.049
Eye Corrosion:	0.004
Eye Irritation:	0.033
Respiratory Toxicity:	0.633

Download Data

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

Natural Product: NPC146388

Natural Product ID:	NPC146388
*Common Name:**	Kamolonol
IUPAC Name:	7-[[(1R,2R,4R,4aS,5R,8aS)-4-hydroxy-1,2,4a,5-tetramethyl-6-oxo-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methoxy]chromen-2-one
Synonyms:	Kamolonol
Standard InCHIKey:	XYUJBOZUFFMPGO-ZWJXAUIJSA-N
Standard InCHI:	InChI=1S/C24H30O5/c1-14-11-21(26)24(4)15(2)18(25)8-9-20(24)23(14,3)13-28-17-7-5-16-6-10-22(27)29-19(16)12-17/h5-7,10,12,14-15,20-21,26H,8-9,11,13H2,1-4H3/t14-,15+,20+,21-,23-,24-/m1/s1
SMILES:	C[C@@H]1C[C@H]([C@]2(C)[C@@H](C)C(=O)CC[C@H]2[C@]1(C)COc1ccc2ccc(=O)oc2c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077965
PubChem CID:	46883037
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins 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
NPO3083	Ferula assafoetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3083	Ferula assafoetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3083	Ferula assafoetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[511502]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[511502]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[511502]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[511502]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[511502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17.92	ug.mL-1	PMID[511502]

☑ 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 NPC146388 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	384
0.1-0.2	1506
0.2-0.3	2985
0.3-0.4	6671
0.4-0.5	10424
0.5-0.6	6395
0.6-0.7	5530
0.7-0.8	6594
0.8-0.85	1911
0.85-0.9	274
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC146014
0.9433	High Similarity	NPC155552
0.9433	High Similarity	NPC138149
0.9366	High Similarity	NPC93640
0.9366	High Similarity	NPC20631
0.9236	High Similarity	NPC251372
0.922	High Similarity	NPC131198
0.9155	High Similarity	NPC307883
0.9085	High Similarity	NPC306365
0.8912	High Similarity	NPC71739
0.8904	High Similarity	NPC229916
0.8774	High Similarity	NPC4950
0.8733	High Similarity	NPC142863
0.8716	High Similarity	NPC3732
0.871	High Similarity	NPC158542
0.8681	High Similarity	NPC61499
0.8671	High Similarity	NPC54503
0.8671	High Similarity	NPC55147
0.8667	High Similarity	NPC286038
0.8658	High Similarity	NPC475719
0.8658	High Similarity	NPC101255
0.8658	High Similarity	NPC43716
0.8658	High Similarity	NPC295696
0.8654	High Similarity	NPC239118
0.8654	High Similarity	NPC218818
0.8639	High Similarity	NPC310370
0.8639	High Similarity	NPC472523
0.8639	High Similarity	NPC183642
0.8634	High Similarity	NPC193698
0.8627	High Similarity	NPC48671
0.8618	High Similarity	NPC103116
0.8609	High Similarity	NPC66991
0.8571	High Similarity	NPC71903
0.8562	High Similarity	NPC140133
0.8562	High Similarity	NPC14697
0.8562	High Similarity	NPC471069
0.8562	High Similarity	NPC471068
0.8553	High Similarity	NPC469395
0.8542	High Similarity	NPC31849
0.8533	High Similarity	NPC106126
0.8533	High Similarity	NPC108994
0.8514	High Similarity	NPC287286
0.8514	High Similarity	NPC170812
0.8503	High Similarity	NPC327612
0.8503	High Similarity	NPC471072
0.8503	High Similarity	NPC73078
0.8503	High Similarity	NPC471070
0.8503	High Similarity	NPC148738
0.8503	High Similarity	NPC471071
0.8503	High Similarity	NPC319870
0.8491	Intermediate Similarity	NPC473022
0.8481	Intermediate Similarity	NPC472618
0.8477	Intermediate Similarity	NPC471608
0.8471	Intermediate Similarity	NPC474611
0.8447	Intermediate Similarity	NPC125465
0.8447	Intermediate Similarity	NPC120857
0.8447	Intermediate Similarity	NPC85047
0.8447	Intermediate Similarity	NPC17274
0.8446	Intermediate Similarity	NPC312881
0.8442	Intermediate Similarity	NPC474735
0.8442	Intermediate Similarity	NPC119252
0.8435	Intermediate Similarity	NPC155963
0.8425	Intermediate Similarity	NPC229128
0.8418	Intermediate Similarity	NPC226287
0.8411	Intermediate Similarity	NPC169942
0.8411	Intermediate Similarity	NPC469701
0.8392	Intermediate Similarity	NPC474289
0.8389	Intermediate Similarity	NPC152771
0.8389	Intermediate Similarity	NPC195357
0.8387	Intermediate Similarity	NPC312549
0.8387	Intermediate Similarity	NPC316960
0.8387	Intermediate Similarity	NPC305965
0.8387	Intermediate Similarity	NPC209142
0.8387	Intermediate Similarity	NPC317715
0.8387	Intermediate Similarity	NPC78835
0.8387	Intermediate Similarity	NPC148945
0.8387	Intermediate Similarity	NPC309512
0.8387	Intermediate Similarity	NPC204561
0.838	Intermediate Similarity	NPC224774
0.838	Intermediate Similarity	NPC121740
0.838	Intermediate Similarity	NPC258567
0.8378	Intermediate Similarity	NPC37428
0.8378	Intermediate Similarity	NPC279573
0.8378	Intermediate Similarity	NPC137262
0.8378	Intermediate Similarity	NPC278600
0.8378	Intermediate Similarity	NPC47040
0.8378	Intermediate Similarity	NPC35501
0.8378	Intermediate Similarity	NPC151946
0.8378	Intermediate Similarity	NPC144512
0.8378	Intermediate Similarity	NPC221046
0.8378	Intermediate Similarity	NPC211110
0.8377	Intermediate Similarity	NPC19238
0.8377	Intermediate Similarity	NPC212257
0.8367	Intermediate Similarity	NPC26954
0.8367	Intermediate Similarity	NPC246177
0.8367	Intermediate Similarity	NPC128529
0.8367	Intermediate Similarity	NPC149320
0.8367	Intermediate Similarity	NPC283019
0.8367	Intermediate Similarity	NPC55615
0.8367	Intermediate Similarity	NPC317045
0.8367	Intermediate Similarity	NPC471630
0.8367	Intermediate Similarity	NPC177281
0.8367	Intermediate Similarity	NPC38099
0.8367	Intermediate Similarity	NPC476455
0.8367	Intermediate Similarity	NPC283331
0.8367	Intermediate Similarity	NPC160727
0.8356	Intermediate Similarity	NPC224475
0.8356	Intermediate Similarity	NPC62366
0.8356	Intermediate Similarity	NPC50896
0.8356	Intermediate Similarity	NPC326600
0.8356	Intermediate Similarity	NPC204353
0.8356	Intermediate Similarity	NPC180716
0.8356	Intermediate Similarity	NPC213173
0.8354	Intermediate Similarity	NPC472620
0.8345	Intermediate Similarity	NPC175159
0.8345	Intermediate Similarity	NPC194277
0.8344	Intermediate Similarity	NPC20734
0.8344	Intermediate Similarity	NPC54903
0.8344	Intermediate Similarity	NPC472619
0.8344	Intermediate Similarity	NPC286074
0.8333	Intermediate Similarity	NPC469394
0.8333	Intermediate Similarity	NPC223720
0.8333	Intermediate Similarity	NPC113098
0.8323	Intermediate Similarity	NPC225854
0.8323	Intermediate Similarity	NPC476295
0.8323	Intermediate Similarity	NPC231668
0.8323	Intermediate Similarity	NPC474660
0.8322	Intermediate Similarity	NPC469453
0.8322	Intermediate Similarity	NPC185066
0.8313	Intermediate Similarity	NPC97812
0.8312	Intermediate Similarity	NPC228012
0.8311	Intermediate Similarity	NPC153818
0.8311	Intermediate Similarity	NPC472516
0.8311	Intermediate Similarity	NPC232246
0.8311	Intermediate Similarity	NPC309452
0.8302	Intermediate Similarity	NPC186113
0.8302	Intermediate Similarity	NPC472299
0.8302	Intermediate Similarity	NPC470339
0.8302	Intermediate Similarity	NPC472617
0.8301	Intermediate Similarity	NPC469758
0.8301	Intermediate Similarity	NPC470322
0.8301	Intermediate Similarity	NPC154217
0.8299	Intermediate Similarity	NPC86892
0.8299	Intermediate Similarity	NPC472525
0.8299	Intermediate Similarity	NPC281241
0.8299	Intermediate Similarity	NPC471625
0.8299	Intermediate Similarity	NPC471909
0.8299	Intermediate Similarity	NPC472424
0.8291	Intermediate Similarity	NPC304692
0.8291	Intermediate Similarity	NPC166116
0.8291	Intermediate Similarity	NPC55463
0.8288	Intermediate Similarity	NPC291551
0.8288	Intermediate Similarity	NPC205797
0.8288	Intermediate Similarity	NPC241165
0.8288	Intermediate Similarity	NPC142563
0.8288	Intermediate Similarity	NPC469965
0.8288	Intermediate Similarity	NPC83535
0.8288	Intermediate Similarity	NPC1220
0.8288	Intermediate Similarity	NPC141822
0.8282	Intermediate Similarity	NPC472622
0.828	Intermediate Similarity	NPC268484
0.828	Intermediate Similarity	NPC60084
0.8276	Intermediate Similarity	NPC267336
0.8276	Intermediate Similarity	NPC472517
0.8276	Intermediate Similarity	NPC272650
0.8276	Intermediate Similarity	NPC29734
0.8269	Intermediate Similarity	NPC290671
0.8269	Intermediate Similarity	NPC189773
0.8269	Intermediate Similarity	NPC473131
0.8269	Intermediate Similarity	NPC39819
0.8269	Intermediate Similarity	NPC470675
0.8267	Intermediate Similarity	NPC136095
0.8267	Intermediate Similarity	NPC472515
0.8264	Intermediate Similarity	NPC168710
0.8261	Intermediate Similarity	NPC249070
0.8258	Intermediate Similarity	NPC104236
0.8258	Intermediate Similarity	NPC471114
0.8258	Intermediate Similarity	NPC164205
0.8253	Intermediate Similarity	NPC294149
0.825	Intermediate Similarity	NPC114147
0.825	Intermediate Similarity	NPC79571
0.825	Intermediate Similarity	NPC472055
0.8247	Intermediate Similarity	NPC325032
0.8247	Intermediate Similarity	NPC474108
0.8247	Intermediate Similarity	NPC77903
0.8247	Intermediate Similarity	NPC177995
0.8247	Intermediate Similarity	NPC300988
0.8247	Intermediate Similarity	NPC477483
0.8247	Intermediate Similarity	NPC10990
0.8247	Intermediate Similarity	NPC17101
0.8243	Intermediate Similarity	NPC223616
0.8243	Intermediate Similarity	NPC224543
0.8243	Intermediate Similarity	NPC104796
0.8243	Intermediate Similarity	NPC188380
0.8243	Intermediate Similarity	NPC78746
0.8243	Intermediate Similarity	NPC266245
0.8239	Intermediate Similarity	NPC471827
0.8239	Intermediate Similarity	NPC123153
0.8239	Intermediate Similarity	NPC471828
0.8239	Intermediate Similarity	NPC272196

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 NPC146388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	928
0.2-0.3	1598
0.3-0.4	2515
0.4-0.5	2119
0.5-0.6	1087
0.6-0.7	381
0.7-0.8	162
0.8-0.85	27
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8456	Intermediate Similarity	NPD3750	Approved
0.8456	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD3748	Approved
0.8301	Intermediate Similarity	NPD6273	Approved
0.8288	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD5124	Phase 1
0.828	Intermediate Similarity	NPD7819	Suspended
0.8235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5844	Phase 1
0.8207	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7411	Suspended
0.8112	Intermediate Similarity	NPD2797	Approved
0.8092	Intermediate Similarity	NPD4628	Phase 3
0.8089	Intermediate Similarity	NPD6599	Discontinued
0.8086	Intermediate Similarity	NPD8127	Discontinued
0.8082	Intermediate Similarity	NPD3268	Approved
0.8067	Intermediate Similarity	NPD2796	Approved
0.8067	Intermediate Similarity	NPD6099	Approved
0.8067	Intermediate Similarity	NPD6100	Approved
0.8063	Intermediate Similarity	NPD7768	Phase 2
0.805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD37	Approved
0.7973	Intermediate Similarity	NPD4140	Approved
0.7959	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4966	Approved
0.795	Intermediate Similarity	NPD4967	Phase 2
0.795	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4965	Approved
0.7945	Intermediate Similarity	NPD4908	Phase 1
0.7905	Intermediate Similarity	NPD8032	Phase 2
0.7901	Intermediate Similarity	NPD3749	Approved
0.7901	Intermediate Similarity	NPD7075	Discontinued
0.7898	Intermediate Similarity	NPD5403	Approved
0.7888	Intermediate Similarity	NPD5402	Approved
0.7885	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5401	Approved
0.7885	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2799	Discontinued
0.7862	Intermediate Similarity	NPD3267	Approved
0.7862	Intermediate Similarity	NPD3266	Approved
0.7862	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD7003	Approved
0.7843	Intermediate Similarity	NPD1549	Phase 2
0.7843	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD422	Phase 1
0.7831	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6799	Approved
0.7818	Intermediate Similarity	NPD7229	Phase 3
0.7812	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3226	Approved
0.7791	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1510	Phase 2
0.7758	Intermediate Similarity	NPD6959	Discontinued
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.7744	Intermediate Similarity	NPD6234	Discontinued
0.7742	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1296	Phase 2
0.7718	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6798	Discontinued
0.7716	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD5494	Approved
0.7688	Intermediate Similarity	NPD7458	Discontinued
0.7682	Intermediate Similarity	NPD6355	Discontinued
0.7679	Intermediate Similarity	NPD7473	Discontinued
0.7677	Intermediate Similarity	NPD1652	Phase 2
0.7673	Intermediate Similarity	NPD920	Approved
0.7671	Intermediate Similarity	NPD3225	Approved
0.7669	Intermediate Similarity	NPD3817	Phase 2
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD2534	Approved
0.7658	Intermediate Similarity	NPD2532	Approved
0.7658	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD7033	Discontinued
0.7647	Intermediate Similarity	NPD4308	Phase 3
0.7633	Intermediate Similarity	NPD7228	Approved
0.7628	Intermediate Similarity	NPD8166	Discontinued
0.7605	Intermediate Similarity	NPD6232	Discontinued
0.7602	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2313	Discontinued
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.7569	Intermediate Similarity	NPD1778	Approved
0.7568	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1243	Approved
0.7561	Intermediate Similarity	NPD4288	Approved
0.756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6559	Discontinued
0.7548	Intermediate Similarity	NPD6005	Phase 3
0.7548	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6002	Phase 3
0.7548	Intermediate Similarity	NPD6004	Phase 3
0.7547	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1934	Approved
0.7534	Intermediate Similarity	NPD1608	Approved
0.7532	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3818	Discontinued
0.7516	Intermediate Similarity	NPD4110	Phase 3
0.7516	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD4307	Phase 2
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7468	Intermediate Similarity	NPD7097	Phase 1
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7457	Intermediate Similarity	NPD7240	Approved
0.7452	Intermediate Similarity	NPD2800	Approved
0.7443	Intermediate Similarity	NPD8434	Phase 2
0.7436	Intermediate Similarity	NPD5763	Approved
0.7436	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5762	Approved
0.7434	Intermediate Similarity	NPD6233	Phase 2
0.7432	Intermediate Similarity	NPD1283	Approved
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7417	Intermediate Similarity	NPD4625	Phase 3
0.7417	Intermediate Similarity	NPD7095	Approved
0.7414	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3882	Suspended
0.7407	Intermediate Similarity	NPD1653	Approved
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7394	Intermediate Similarity	NPD5761	Phase 2
0.7394	Intermediate Similarity	NPD5760	Phase 2
0.7386	Intermediate Similarity	NPD4060	Phase 1
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7054	Approved
0.7379	Intermediate Similarity	NPD5691	Approved
0.7375	Intermediate Similarity	NPD1511	Approved
0.7372	Intermediate Similarity	NPD4476	Approved
0.7372	Intermediate Similarity	NPD4477	Approved
0.7368	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3764	Approved
0.7365	Intermediate Similarity	NPD6971	Discontinued
0.7365	Intermediate Similarity	NPD4749	Approved
0.7362	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7074	Phase 3
0.7341	Intermediate Similarity	NPD7472	Approved
0.7338	Intermediate Similarity	NPD5735	Approved
0.7333	Intermediate Similarity	NPD2798	Approved
0.7329	Intermediate Similarity	NPD17	Approved
0.7329	Intermediate Similarity	NPD4626	Approved
0.7321	Intermediate Similarity	NPD919	Approved
0.732	Intermediate Similarity	NPD6663	Approved
0.7299	Intermediate Similarity	NPD6797	Phase 2
0.7299	Intermediate Similarity	NPD5953	Discontinued
0.7297	Intermediate Similarity	NPD9717	Approved
0.7285	Intermediate Similarity	NPD5736	Approved
0.7284	Intermediate Similarity	NPD1512	Approved
0.7278	Intermediate Similarity	NPD2424	Discontinued
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2979	Phase 3
0.7273	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1203	Approved
0.7261	Intermediate Similarity	NPD2438	Suspended
0.726	Intermediate Similarity	NPD5585	Approved
0.7257	Intermediate Similarity	NPD7251	Discontinued
0.7254	Intermediate Similarity	NPD5535	Approved
0.7248	Intermediate Similarity	NPD5327	Phase 3
0.7239	Intermediate Similarity	NPD7427	Discontinued
0.7237	Intermediate Similarity	NPD2614	Approved
0.7233	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1281	Approved
0.7226	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7177	Discontinued
0.7216	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7549	Discontinued
0.7216	Intermediate Similarity	NPD7808	Phase 3
0.7205	Intermediate Similarity	NPD6667	Approved
0.7205	Intermediate Similarity	NPD7236	Approved
0.7205	Intermediate Similarity	NPD6666	Approved
0.7203	Intermediate Similarity	NPD1241	Discontinued
0.72	Intermediate Similarity	NPD8651	Approved
0.7197	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1894	Discontinued
0.7184	Intermediate Similarity	NPD7286	Phase 2
0.7181	Intermediate Similarity	NPD3972	Approved
0.7179	Intermediate Similarity	NPD6651	Approved
0.7178	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6746	Phase 2
0.7171	Intermediate Similarity	NPD2861	Phase 2
0.717	Intermediate Similarity	NPD4534	Discontinued
0.7169	Intermediate Similarity	NPD6677	Suspended

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