NPASS Compound

Structure

NPC470740 OpenBabel07101718302D 26 28 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9973 -0.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9960 -0.6918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4161 0.8188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6390 0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 1.4142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 0.2742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 26 1 0 0 0 0 9 15 1 0 0 0 0 9 17 2 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 26 1 0 0 0 0 13 20 1 6 0 0 0 14 18 1 0 0 0 0 15 22 2 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	3.254
LogD:	3.064
LogS:	-4.54
# Rotatable Bonds:	5
TPSA:	73.58
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	4.473
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.943
MDCK Permeability:	3.747638038475998e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.292
30% Bioavailability (F30%):	0.428

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	81.98512268066406%
Volume Distribution (VD):	0.604
Pgp-substrate:	9.655689239501953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.182
CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.555
CYP2C19-substrate:	0.655
CYP2C9-inhibitor:	0.523
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.632

ADMET: Excretion

Clearance (CL):	15.089
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.787
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.188
Carcinogencity:	0.958
Eye Corrosion:	0.004
Eye Irritation:	0.013
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: NPC470740

Natural Product ID:	NPC470740
*Common Name:**	Crassifolin C
IUPAC Name:	methyl (1S,5S,6R)-5-[2-(furan-3-yl)-2-oxoethyl]-1,5,6-trimethyl-3-oxo-6,7-dihydro-2H-naphthalene-1-carboxylate
Synonyms:	Crassifolin C
Standard InCHIKey:	TWTOVEROIIRYEO-UBWHGVKJSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-13-5-6-16-17(9-15(22)10-21(16,3)19(24)25-4)20(13,2)11-18(23)14-7-8-26-12-14/h6-9,12-13H,5,10-11H2,1-4H3/t13-,20+,21+/m1/s1
SMILES:	COC(=O)[C@@]1(C)CC(=O)C=C2C1=CC[C@H]([C@]2(C)CC(=O)c1cocc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208212
PubChem CID:	71454345
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO32991	croton crassifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194476]
NPO32991	croton crassifolius	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28150949]
NPO32991	croton crassifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32003565]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IC50	=	50.0	ug.mL-1	PMID[542977]

☑ 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 NPC470740 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	301
0.1-0.2	1459
0.2-0.3	3562
0.3-0.4	8324
0.4-0.5	12184
0.5-0.6	8653
0.6-0.7	7275
0.7-0.8	811
0.8-0.85	103
0.85-0.9	19
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9466	High Similarity	NPC236532
0.9462	High Similarity	NPC146872
0.9098	High Similarity	NPC42400
0.9091	High Similarity	NPC92941
0.903	High Similarity	NPC220094
0.8955	High Similarity	NPC470742
0.8931	High Similarity	NPC298190
0.8915	High Similarity	NPC83178
0.8815	High Similarity	NPC310830
0.876	High Similarity	NPC179354
0.875	High Similarity	NPC476943
0.875	High Similarity	NPC16922
0.8723	High Similarity	NPC10088
0.8702	High Similarity	NPC112706
0.8702	High Similarity	NPC207294
0.8652	High Similarity	NPC233763
0.8652	High Similarity	NPC276676
0.8651	High Similarity	NPC243704
0.8643	High Similarity	NPC142113
0.864	High Similarity	NPC45536
0.8636	High Similarity	NPC208389
0.8633	High Similarity	NPC473152
0.8571	High Similarity	NPC470741
0.8571	High Similarity	NPC267632
0.8561	High Similarity	NPC477039
0.8551	High Similarity	NPC474722
0.855	High Similarity	NPC46536
0.855	High Similarity	NPC74612
0.855	High Similarity	NPC138139
0.8538	High Similarity	NPC65735
0.8538	High Similarity	NPC188377
0.8519	High Similarity	NPC471006
0.85	High Similarity	NPC52412
0.8485	Intermediate Similarity	NPC95567
0.8485	Intermediate Similarity	NPC319140
0.8462	Intermediate Similarity	NPC224418
0.8444	Intermediate Similarity	NPC471817
0.8438	Intermediate Similarity	NPC473969
0.8433	Intermediate Similarity	NPC21460
0.8421	Intermediate Similarity	NPC477966
0.8421	Intermediate Similarity	NPC477123
0.8417	Intermediate Similarity	NPC90953
0.8409	Intermediate Similarity	NPC23086
0.8406	Intermediate Similarity	NPC307401
0.8397	Intermediate Similarity	NPC243269
0.8394	Intermediate Similarity	NPC158525
0.8385	Intermediate Similarity	NPC317217
0.838	Intermediate Similarity	NPC199044
0.838	Intermediate Similarity	NPC238843
0.837	Intermediate Similarity	NPC89133
0.837	Intermediate Similarity	NPC136340
0.8358	Intermediate Similarity	NPC59502
0.8357	Intermediate Similarity	NPC56197
0.8333	Intermediate Similarity	NPC473885
0.8333	Intermediate Similarity	NPC471074
0.831	Intermediate Similarity	NPC223415
0.8308	Intermediate Similarity	NPC79557
0.8308	Intermediate Similarity	NPC1848
0.8288	Intermediate Similarity	NPC46551
0.8286	Intermediate Similarity	NPC202260
0.8284	Intermediate Similarity	NPC327527
0.8284	Intermediate Similarity	NPC477040
0.8284	Intermediate Similarity	NPC476917
0.8284	Intermediate Similarity	NPC26532
0.8281	Intermediate Similarity	NPC131801
0.8268	Intermediate Similarity	NPC150895
0.8264	Intermediate Similarity	NPC262198
0.8264	Intermediate Similarity	NPC346
0.8264	Intermediate Similarity	NPC471292
0.8258	Intermediate Similarity	NPC477038
0.8258	Intermediate Similarity	NPC477965
0.8252	Intermediate Similarity	NPC476944
0.8248	Intermediate Similarity	NPC474425
0.8248	Intermediate Similarity	NPC474407
0.8248	Intermediate Similarity	NPC474426
0.8244	Intermediate Similarity	NPC36255
0.8244	Intermediate Similarity	NPC477967
0.8235	Intermediate Similarity	NPC61788
0.8231	Intermediate Similarity	NPC144010
0.8227	Intermediate Similarity	NPC148374
0.8217	Intermediate Similarity	NPC87466
0.8209	Intermediate Similarity	NPC290955
0.8209	Intermediate Similarity	NPC246392
0.8207	Intermediate Similarity	NPC250228
0.8201	Intermediate Similarity	NPC46896
0.8195	Intermediate Similarity	NPC230979
0.8169	Intermediate Similarity	NPC20500
0.8168	Intermediate Similarity	NPC97566
0.8163	Intermediate Similarity	NPC469335
0.8163	Intermediate Similarity	NPC159927
0.8162	Intermediate Similarity	NPC476925
0.8151	Intermediate Similarity	NPC476941
0.8151	Intermediate Similarity	NPC476942
0.8148	Intermediate Similarity	NPC279877
0.8143	Intermediate Similarity	NPC170604
0.8143	Intermediate Similarity	NPC215109
0.814	Intermediate Similarity	NPC144745
0.814	Intermediate Similarity	NPC208906
0.8138	Intermediate Similarity	NPC62799
0.8129	Intermediate Similarity	NPC159786
0.8121	Intermediate Similarity	NPC471863
0.812	Intermediate Similarity	NPC83115
0.812	Intermediate Similarity	NPC130275
0.8116	Intermediate Similarity	NPC218838
0.8116	Intermediate Similarity	NPC293253
0.8099	Intermediate Similarity	NPC90296
0.8095	Intermediate Similarity	NPC329180
0.8088	Intermediate Similarity	NPC198904
0.8085	Intermediate Similarity	NPC472376
0.8085	Intermediate Similarity	NPC177262
0.8082	Intermediate Similarity	NPC476937
0.8082	Intermediate Similarity	NPC476938
0.8082	Intermediate Similarity	NPC221809
0.8082	Intermediate Similarity	NPC470941
0.8079	Intermediate Similarity	NPC81405
0.8069	Intermediate Similarity	NPC34056
0.8069	Intermediate Similarity	NPC56731
0.8067	Intermediate Similarity	NPC281258
0.806	Intermediate Similarity	NPC474829
0.806	Intermediate Similarity	NPC75557
0.806	Intermediate Similarity	NPC71274
0.8058	Intermediate Similarity	NPC471998
0.8056	Intermediate Similarity	NPC80635
0.8054	Intermediate Similarity	NPC44577
0.8041	Intermediate Similarity	NPC477404
0.8041	Intermediate Similarity	NPC156189
0.8041	Intermediate Similarity	NPC196864
0.8041	Intermediate Similarity	NPC472298
0.8028	Intermediate Similarity	NPC474615
0.8026	Intermediate Similarity	NPC474932
0.8026	Intermediate Similarity	NPC140952
0.8015	Intermediate Similarity	NPC474438
0.8015	Intermediate Similarity	NPC474279
0.8014	Intermediate Similarity	NPC186626
0.8	Intermediate Similarity	NPC471521
0.8	Intermediate Similarity	NPC329922
0.8	Intermediate Similarity	NPC329694
0.8	Intermediate Similarity	NPC30222
0.8	Intermediate Similarity	NPC251865
0.8	Intermediate Similarity	NPC217180
0.8	Intermediate Similarity	NPC473356
0.8	Intermediate Similarity	NPC312525
0.8	Intermediate Similarity	NPC212918
0.8	Intermediate Similarity	NPC474260
0.8	Intermediate Similarity	NPC178932
0.8	Intermediate Similarity	NPC81912
0.8	Intermediate Similarity	NPC86935
0.7987	Intermediate Similarity	NPC240214
0.7987	Intermediate Similarity	NPC272590
0.7986	Intermediate Similarity	NPC121158
0.7985	Intermediate Similarity	NPC118853
0.7984	Intermediate Similarity	NPC28054
0.7984	Intermediate Similarity	NPC205523
0.7973	Intermediate Similarity	NPC195325
0.7973	Intermediate Similarity	NPC472654
0.7973	Intermediate Similarity	NPC234494
0.7973	Intermediate Similarity	NPC471001
0.7959	Intermediate Similarity	NPC471174
0.7959	Intermediate Similarity	NPC281398
0.7959	Intermediate Similarity	NPC71821
0.7956	Intermediate Similarity	NPC223063
0.7956	Intermediate Similarity	NPC120836
0.7953	Intermediate Similarity	NPC105249
0.7947	Intermediate Similarity	NPC469850
0.7947	Intermediate Similarity	NPC25351
0.7947	Intermediate Similarity	NPC35000
0.7947	Intermediate Similarity	NPC469336
0.7947	Intermediate Similarity	NPC264943
0.7945	Intermediate Similarity	NPC185456
0.7941	Intermediate Similarity	NPC474830
0.7941	Intermediate Similarity	NPC476016
0.7933	Intermediate Similarity	NPC246164
0.7933	Intermediate Similarity	NPC469503
0.7933	Intermediate Similarity	NPC75906
0.7931	Intermediate Similarity	NPC476946
0.792	Intermediate Similarity	NPC140688
0.7919	Intermediate Similarity	NPC476122
0.7919	Intermediate Similarity	NPC476936
0.7919	Intermediate Similarity	NPC5180
0.7919	Intermediate Similarity	NPC470997
0.7917	Intermediate Similarity	NPC205765
0.7914	Intermediate Similarity	NPC473982
0.7914	Intermediate Similarity	NPC471995
0.791	Intermediate Similarity	NPC476351
0.7905	Intermediate Similarity	NPC19747
0.7905	Intermediate Similarity	NPC93666
0.7895	Intermediate Similarity	NPC60973
0.7895	Intermediate Similarity	NPC209364
0.7895	Intermediate Similarity	NPC469485
0.7883	Intermediate Similarity	NPC329707
0.7881	Intermediate Similarity	NPC57998
0.7879	Intermediate Similarity	NPC244862
0.7879	Intermediate Similarity	NPC67345
0.7877	Intermediate Similarity	NPC117674
0.7877	Intermediate Similarity	NPC84479
0.7872	Intermediate Similarity	NPC476947
0.7867	Intermediate Similarity	NPC18135
0.7867	Intermediate Similarity	NPC116717
0.7867	Intermediate Similarity	NPC291150
0.7863	Intermediate Similarity	NPC227660

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 NPC470740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	1023
0.2-0.3	1924
0.3-0.4	2671
0.4-0.5	2090
0.5-0.6	908
0.6-0.7	238
0.7-0.8	24
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
0.7902	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1471	Phase 3
0.7639	Intermediate Similarity	NPD2799	Discontinued
0.7447	Intermediate Similarity	NPD6832	Phase 2
0.7434	Intermediate Similarity	NPD920	Approved
0.7415	Intermediate Similarity	NPD2344	Approved
0.7372	Intermediate Similarity	NPD5761	Phase 2
0.7372	Intermediate Similarity	NPD5760	Phase 2
0.7343	Intermediate Similarity	NPD2313	Discontinued
0.7303	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2346	Discontinued
0.7285	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3972	Approved
0.7219	Intermediate Similarity	NPD2309	Approved
0.7219	Intermediate Similarity	NPD8434	Phase 2
0.7195	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2798	Approved
0.7164	Intermediate Similarity	NPD1241	Discontinued
0.7163	Intermediate Similarity	NPD1876	Approved
0.716	Intermediate Similarity	NPD6808	Phase 2
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD6273	Approved
0.7089	Intermediate Similarity	NPD6280	Approved
0.7089	Intermediate Similarity	NPD6279	Approved
0.7086	Intermediate Similarity	NPD1243	Approved
0.7075	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6599	Discontinued
0.7063	Intermediate Similarity	NPD1019	Discontinued
0.7055	Intermediate Similarity	NPD8032	Phase 2
0.705	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD1551	Phase 2
0.6978	Remote Similarity	NPD5585	Approved
0.6975	Remote Similarity	NPD919	Approved
0.694	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6765	Approved
0.6923	Remote Similarity	NPD6764	Approved
0.6894	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4307	Phase 2
0.6887	Remote Similarity	NPD2935	Discontinued
0.6887	Remote Similarity	NPD2796	Approved
0.6875	Remote Similarity	NPD3266	Approved
0.6875	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1203	Approved
0.6875	Remote Similarity	NPD3267	Approved
0.6863	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2800	Approved
0.6846	Remote Similarity	NPD1933	Approved
0.6832	Remote Similarity	NPD7819	Suspended
0.6828	Remote Similarity	NPD5647	Approved
0.6821	Remote Similarity	NPD3748	Approved
0.6818	Remote Similarity	NPD7003	Approved
0.6818	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD17	Approved
0.6795	Remote Similarity	NPD6799	Approved
0.6792	Remote Similarity	NPD7458	Discontinued
0.6791	Remote Similarity	NPD2182	Approved
0.6779	Remote Similarity	NPD2979	Phase 3
0.6763	Remote Similarity	NPD6785	Approved
0.6763	Remote Similarity	NPD6784	Approved
0.6759	Remote Similarity	NPD2797	Approved
0.6757	Remote Similarity	NPD411	Approved
0.6757	Remote Similarity	NPD3268	Approved
0.6736	Remote Similarity	NPD4359	Approved
0.6733	Remote Similarity	NPD447	Suspended
0.6733	Remote Similarity	NPD6355	Discontinued
0.6728	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5494	Approved
0.6725	Remote Similarity	NPD6559	Discontinued
0.6713	Remote Similarity	NPD1281	Approved
0.6711	Remote Similarity	NPD4308	Phase 3
0.671	Remote Similarity	NPD4110	Phase 3
0.671	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7411	Suspended
0.6707	Remote Similarity	NPD3749	Approved
0.6707	Remote Similarity	NPD3926	Phase 2
0.6689	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1247	Approved
0.6687	Remote Similarity	NPD2296	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD3887	Approved
0.6646	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD2534	Approved
0.6646	Remote Similarity	NPD2532	Approved
0.6646	Remote Similarity	NPD2533	Approved
0.6642	Remote Similarity	NPD3134	Approved
0.6623	Remote Similarity	NPD4618	Approved
0.6623	Remote Similarity	NPD4622	Approved
0.662	Remote Similarity	NPD5691	Approved
0.6606	Remote Similarity	NPD7075	Discontinued
0.6605	Remote Similarity	NPD5890	Approved
0.6605	Remote Similarity	NPD5889	Approved
0.6603	Remote Similarity	NPD3750	Approved
0.6597	Remote Similarity	NPD6287	Discontinued
0.6575	Remote Similarity	NPD1283	Approved
0.6573	Remote Similarity	NPD1778	Approved
0.6564	Remote Similarity	NPD6801	Discontinued
0.6562	Remote Similarity	NPD3873	Phase 3
0.6562	Remote Similarity	NPD5403	Approved
0.6562	Remote Similarity	NPD3869	Phase 3
0.6558	Remote Similarity	NPD2531	Phase 2
0.6558	Remote Similarity	NPD2438	Suspended
0.6556	Remote Similarity	NPD4140	Approved
0.6556	Remote Similarity	NPD3142	Approved
0.6556	Remote Similarity	NPD3140	Approved
0.6548	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5401	Approved
0.6536	Remote Similarity	NPD5688	Approved
0.6536	Remote Similarity	NPD5689	Approved
0.6533	Remote Similarity	NPD3764	Approved
0.6528	Remote Similarity	NPD3496	Discontinued
0.6528	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD9493	Approved
0.6522	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6004	Phase 3
0.6516	Remote Similarity	NPD6002	Phase 3
0.6516	Remote Similarity	NPD2353	Approved
0.6516	Remote Similarity	NPD6005	Phase 3
0.6516	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1651	Approved
0.6497	Remote Similarity	NPD8166	Discontinued
0.6493	Remote Similarity	NPD164	Approved
0.649	Remote Similarity	NPD4870	Approved
0.6485	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5402	Approved
0.6475	Remote Similarity	NPD5535	Approved
0.6474	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1549	Phase 2
0.6471	Remote Similarity	NPD1358	Approved
0.6471	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4477	Approved
0.6452	Remote Similarity	NPD4476	Approved
0.6446	Remote Similarity	NPD3882	Suspended
0.6442	Remote Similarity	NPD6585	Discontinued
0.6442	Remote Similarity	NPD7028	Phase 2
0.6438	Remote Similarity	NPD4661	Approved
0.6438	Remote Similarity	NPD4662	Approved
0.6434	Remote Similarity	NPD1894	Discontinued
0.6424	Remote Similarity	NPD6798	Discontinued
0.641	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6873	Phase 2
0.64	Remote Similarity	NPD2614	Approved
0.6395	Remote Similarity	NPD5327	Phase 3
0.6391	Remote Similarity	NPD8127	Discontinued
0.6387	Remote Similarity	NPD1510	Phase 2
0.6387	Remote Similarity	NPD7033	Discontinued
0.6386	Remote Similarity	NPD3817	Phase 2
0.6379	Remote Similarity	NPD5953	Discontinued
0.6369	Remote Similarity	NPD4534	Discontinued
0.6364	Remote Similarity	NPD6844	Discontinued
0.6364	Remote Similarity	NPD1607	Approved
0.6364	Remote Similarity	NPD8312	Approved
0.6364	Remote Similarity	NPD8313	Approved
0.6364	Remote Similarity	NPD6651	Approved
0.6358	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7095	Approved
0.6352	Remote Similarity	NPD2354	Approved
0.6352	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4626	Approved
0.634	Remote Similarity	NPD1240	Approved
0.6338	Remote Similarity	NPD7157	Approved
0.6337	Remote Similarity	NPD7473	Discontinued
0.6335	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD9697	Approved
0.6324	Remote Similarity	NPD4107	Approved
0.6323	Remote Similarity	NPD7097	Phase 1
0.6319	Remote Similarity	NPD9545	Approved
0.6316	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1238	Approved
0.6312	Remote Similarity	NPD7236	Approved
0.6312	Remote Similarity	NPD7440	Discontinued
0.6309	Remote Similarity	NPD6362	Approved
0.6309	Remote Similarity	NPD1470	Approved
0.6304	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5049	Phase 3
0.6294	Remote Similarity	NPD405	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4482	Phase 3
0.6275	Remote Similarity	NPD4062	Phase 3
0.6275	Remote Similarity	NPD6233	Phase 2
0.6268	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD2897	Discontinued
0.6266	Remote Similarity	NPD5958	Discontinued
0.6265	Remote Similarity	NPD7317	Phase 3
0.6264	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2067	Discontinued
0.6259	Remote Similarity	NPD1611	Approved
0.6258	Remote Similarity	NPD6653	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