NPASS Compound

Structure

NPC471793 OpenBabel07101718312D 23 25 0 0 1 0 0 0 0 0999 V2000 3.6758 2.6199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2610 0.8570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1462 0.8327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7470 2.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4982 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6270 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 1.4423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8327 0.4808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6654 -0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4982 1.4423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6654 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8327 0.4808 0.0000 C 0 0 1 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 -3.1077 0.8327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 -1.4423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -0.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 4 19 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 6 0 0 0 15 18 1 6 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 2 1 1 0 0 0 18 3 1 1 0 0 0 19 20 1 1 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	2.815
LogD:	2.943
LogS:	-4.241
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	4.978
Fsp3:	0.75
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:	-4.747
MDCK Permeability:	2.6557790988590568e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92
Plasma Protein Binding (PPB):	90.75163269042969%
Volume Distribution (VD):	0.899
Pgp-substrate:	9.797687530517578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.099
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.833

ADMET: Excretion

Clearance (CL):	4.184
Half-life (T1/2):	0.289

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.584
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.851
Skin Sensitization:	0.917
Carcinogencity:	0.752
Eye Corrosion:	0.171
Eye Irritation:	0.519
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: NPC471793

Natural Product ID:	NPC471793
*Common Name:**	Ebractenoid H
IUPAC Name:	(1S,4aS,4bR,7R,8aR,10aS)-7-ethenyl-4a-hydroxy-1-(hydroxymethyl)-1,4b,7-trimethyl-6,8,8a,9,10,10a-hexahydro-5H-phenanthren-2-one
Synonyms:
Standard InCHIKey:	DMNRNXPOMWACEA-NPYRMBCDSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-5-17(2)10-11-19(4)14(12-17)6-7-15-18(3,13-21)16(22)8-9-20(15,19)23/h5,8-9,14-15,21,23H,1,6-7,10-13H2,2-4H3/t14-,15+,17-,18-,19-,20+/m1/s1
SMILES:	C=C[C@]1(C)CC[C@]2(C)[C@H](CC[C@H]3[C@@](C)(CO)C(=O)C=C[C@@]23O)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234210
PubChem CID:	90670333
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids

*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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	19020.0	nM	PMID[495407]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[495408]

☑ 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 NPC471793 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	190
0.1-0.2	1256
0.2-0.3	4842
0.3-0.4	10653
0.4-0.5	12564
0.5-0.6	6885
0.6-0.7	4748
0.7-0.8	1475
0.8-0.85	76
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471791
0.8795	High Similarity	NPC469637
0.8721	High Similarity	NPC476426
0.8621	High Similarity	NPC194417
0.8621	High Similarity	NPC470955
0.8605	High Similarity	NPC476412
0.8539	High Similarity	NPC472477
0.8539	High Similarity	NPC472973
0.8539	High Similarity	NPC472475
0.8523	High Similarity	NPC471792
0.8462	Intermediate Similarity	NPC474807
0.8427	Intermediate Similarity	NPC58271
0.8427	Intermediate Similarity	NPC48107
0.8409	Intermediate Similarity	NPC472974
0.8409	Intermediate Similarity	NPC472986
0.8409	Intermediate Similarity	NPC472985
0.8404	Intermediate Similarity	NPC316598
0.8353	Intermediate Similarity	NPC104120
0.8353	Intermediate Similarity	NPC148685
0.8353	Intermediate Similarity	NPC172013
0.8353	Intermediate Similarity	NPC157895
0.8353	Intermediate Similarity	NPC476809
0.8352	Intermediate Similarity	NPC472978
0.8352	Intermediate Similarity	NPC73457
0.8352	Intermediate Similarity	NPC475806
0.8333	Intermediate Similarity	NPC472489
0.8333	Intermediate Similarity	NPC472983
0.828	Intermediate Similarity	NPC271195
0.8261	Intermediate Similarity	NPC131840
0.8256	Intermediate Similarity	NPC226068
0.8256	Intermediate Similarity	NPC116797
0.8242	Intermediate Similarity	NPC230332
0.8242	Intermediate Similarity	NPC472476
0.8242	Intermediate Similarity	NPC134321
0.8235	Intermediate Similarity	NPC474113
0.8235	Intermediate Similarity	NPC308038
0.8235	Intermediate Similarity	NPC170394
0.8214	Intermediate Similarity	NPC34110
0.8211	Intermediate Similarity	NPC103051
0.8202	Intermediate Similarity	NPC82979
0.8202	Intermediate Similarity	NPC472479
0.8172	Intermediate Similarity	NPC299100
0.8172	Intermediate Similarity	NPC472976
0.8172	Intermediate Similarity	NPC472977
0.8172	Intermediate Similarity	NPC8993
0.8152	Intermediate Similarity	NPC26865
0.8152	Intermediate Similarity	NPC252433
0.8152	Intermediate Similarity	NPC472975
0.814	Intermediate Similarity	NPC472301
0.814	Intermediate Similarity	NPC2482
0.8132	Intermediate Similarity	NPC309603
0.8132	Intermediate Similarity	NPC119416
0.8132	Intermediate Similarity	NPC473999
0.8125	Intermediate Similarity	NPC154072
0.8118	Intermediate Similarity	NPC471409
0.8118	Intermediate Similarity	NPC62336
0.8118	Intermediate Similarity	NPC275494
0.8111	Intermediate Similarity	NPC272039
0.8111	Intermediate Similarity	NPC220930
0.8105	Intermediate Similarity	NPC170131
0.8095	Intermediate Similarity	NPC263582
0.809	Intermediate Similarity	NPC255174
0.809	Intermediate Similarity	NPC70685
0.8085	Intermediate Similarity	NPC474602
0.8085	Intermediate Similarity	NPC259286
0.8085	Intermediate Similarity	NPC180950
0.8085	Intermediate Similarity	NPC290481
0.8085	Intermediate Similarity	NPC476245
0.8065	Intermediate Similarity	NPC476416
0.8065	Intermediate Similarity	NPC109305
0.8065	Intermediate Similarity	NPC474736
0.8061	Intermediate Similarity	NPC131366
0.8046	Intermediate Similarity	NPC14151
0.8046	Intermediate Similarity	NPC473217
0.8046	Intermediate Similarity	NPC121984
0.8043	Intermediate Similarity	NPC128672
0.8043	Intermediate Similarity	NPC48010
0.8041	Intermediate Similarity	NPC282524
0.8041	Intermediate Similarity	NPC470184
0.8023	Intermediate Similarity	NPC281138
0.8022	Intermediate Similarity	NPC158778
0.8022	Intermediate Similarity	NPC472802
0.8022	Intermediate Similarity	NPC474677
0.8022	Intermediate Similarity	NPC72397
0.8022	Intermediate Similarity	NPC476796
0.8021	Intermediate Similarity	NPC478056
0.8	Intermediate Similarity	NPC149550
0.8	Intermediate Similarity	NPC94666
0.8	Intermediate Similarity	NPC257666
0.8	Intermediate Similarity	NPC472488
0.8	Intermediate Similarity	NPC197659
0.8	Intermediate Similarity	NPC85105
0.8	Intermediate Similarity	NPC266193
0.8	Intermediate Similarity	NPC249954
0.8	Intermediate Similarity	NPC117133
0.798	Intermediate Similarity	NPC160843
0.7979	Intermediate Similarity	NPC148964
0.7979	Intermediate Similarity	NPC196227
0.7978	Intermediate Similarity	NPC251170
0.7978	Intermediate Similarity	NPC40687
0.7957	Intermediate Similarity	NPC116726
0.7957	Intermediate Similarity	NPC172101
0.7957	Intermediate Similarity	NPC272746
0.7957	Intermediate Similarity	NPC473998
0.7955	Intermediate Similarity	NPC93590
0.7952	Intermediate Similarity	NPC247586
0.7935	Intermediate Similarity	NPC472970
0.7935	Intermediate Similarity	NPC472971
0.7935	Intermediate Similarity	NPC2983
0.7931	Intermediate Similarity	NPC45495
0.7931	Intermediate Similarity	NPC472478
0.7917	Intermediate Similarity	NPC273269
0.7912	Intermediate Similarity	NPC93778
0.7912	Intermediate Similarity	NPC298904
0.7912	Intermediate Similarity	NPC472484
0.7912	Intermediate Similarity	NPC472482
0.7912	Intermediate Similarity	NPC472481
0.7907	Intermediate Similarity	NPC207772
0.7907	Intermediate Similarity	NPC475994
0.79	Intermediate Similarity	NPC166607
0.7895	Intermediate Similarity	NPC280725
0.7895	Intermediate Similarity	NPC53565
0.7895	Intermediate Similarity	NPC472485
0.7895	Intermediate Similarity	NPC272617
0.7889	Intermediate Similarity	NPC470574
0.7889	Intermediate Similarity	NPC179006
0.7889	Intermediate Similarity	NPC471224
0.7889	Intermediate Similarity	NPC274724
0.7889	Intermediate Similarity	NPC474853
0.7882	Intermediate Similarity	NPC151622
0.7882	Intermediate Similarity	NPC186554
0.7882	Intermediate Similarity	NPC472305
0.7882	Intermediate Similarity	NPC76966
0.7882	Intermediate Similarity	NPC7629
0.7879	Intermediate Similarity	NPC478057
0.7879	Intermediate Similarity	NPC247957
0.7879	Intermediate Similarity	NPC95899
0.7879	Intermediate Similarity	NPC311612
0.7879	Intermediate Similarity	NPC249187
0.7872	Intermediate Similarity	NPC69454
0.7872	Intermediate Similarity	NPC134826
0.7865	Intermediate Similarity	NPC169941
0.7865	Intermediate Similarity	NPC105173
0.7865	Intermediate Similarity	NPC297398
0.7865	Intermediate Similarity	NPC64600
0.7865	Intermediate Similarity	NPC251475
0.7857	Intermediate Similarity	NPC115862
0.7857	Intermediate Similarity	NPC81530
0.7857	Intermediate Similarity	NPC38426
0.7849	Intermediate Similarity	NPC85173
0.7843	Intermediate Similarity	NPC87335
0.7841	Intermediate Similarity	NPC6663
0.7835	Intermediate Similarity	NPC174663
0.7826	Intermediate Similarity	NPC206060
0.7826	Intermediate Similarity	NPC104560
0.7826	Intermediate Similarity	NPC328539
0.7826	Intermediate Similarity	NPC471724
0.7816	Intermediate Similarity	NPC7232
0.7816	Intermediate Similarity	NPC19900
0.7812	Intermediate Similarity	NPC235053
0.7812	Intermediate Similarity	NPC167193
0.7812	Intermediate Similarity	NPC472806
0.7812	Intermediate Similarity	NPC29152
0.7812	Intermediate Similarity	NPC473158
0.7812	Intermediate Similarity	NPC301534
0.7812	Intermediate Similarity	NPC250757
0.7802	Intermediate Similarity	NPC74363
0.7802	Intermediate Similarity	NPC476043
0.7802	Intermediate Similarity	NPC198761
0.7802	Intermediate Similarity	NPC322159
0.7802	Intermediate Similarity	NPC179591
0.7802	Intermediate Similarity	NPC158393
0.7802	Intermediate Similarity	NPC473226
0.7802	Intermediate Similarity	NPC475862
0.7791	Intermediate Similarity	NPC472746
0.7791	Intermediate Similarity	NPC74995
0.7789	Intermediate Similarity	NPC474690
0.7789	Intermediate Similarity	NPC103527
0.7789	Intermediate Similarity	NPC471207
0.7789	Intermediate Similarity	NPC292793
0.7789	Intermediate Similarity	NPC476415
0.7778	Intermediate Similarity	NPC58841
0.7778	Intermediate Similarity	NPC321187
0.7778	Intermediate Similarity	NPC136289
0.7778	Intermediate Similarity	NPC85774
0.7778	Intermediate Similarity	NPC477915
0.7778	Intermediate Similarity	NPC329043
0.7778	Intermediate Similarity	NPC237712
0.7778	Intermediate Similarity	NPC227132
0.7778	Intermediate Similarity	NPC470812
0.7778	Intermediate Similarity	NPC214043
0.7778	Intermediate Similarity	NPC161423
0.7778	Intermediate Similarity	NPC87351
0.7778	Intermediate Similarity	NPC227064
0.7766	Intermediate Similarity	NPC63748
0.7766	Intermediate Similarity	NPC233116
0.7755	Intermediate Similarity	NPC198880
0.7755	Intermediate Similarity	NPC144956
0.7753	Intermediate Similarity	NPC48362
0.7753	Intermediate Similarity	NPC92226

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 NPC471793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1695
0.2-0.3	3814
0.3-0.4	2307
0.4-0.5	708
0.5-0.6	201
0.6-0.7	169
0.7-0.8	79
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8409	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD4519	Discontinued
0.8	Intermediate Similarity	NPD4623	Approved
0.7959	Intermediate Similarity	NPD5211	Phase 2
0.7957	Intermediate Similarity	NPD6079	Approved
0.7872	Intermediate Similarity	NPD4202	Approved
0.78	Intermediate Similarity	NPD5141	Approved
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3666	Approved
0.7778	Intermediate Similarity	NPD3133	Approved
0.7755	Intermediate Similarity	NPD5286	Approved
0.7755	Intermediate Similarity	NPD4696	Approved
0.7755	Intermediate Similarity	NPD5285	Approved
0.7742	Intermediate Similarity	NPD5328	Approved
0.7708	Intermediate Similarity	NPD5210	Approved
0.7708	Intermediate Similarity	NPD4629	Approved
0.7677	Intermediate Similarity	NPD5223	Approved
0.7629	Intermediate Similarity	NPD5221	Approved
0.7629	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD5225	Approved
0.76	Intermediate Similarity	NPD4633	Approved
0.76	Intermediate Similarity	NPD5226	Approved
0.76	Intermediate Similarity	NPD5224	Approved
0.7579	Intermediate Similarity	NPD7515	Phase 2
0.7556	Intermediate Similarity	NPD4223	Phase 3
0.7556	Intermediate Similarity	NPD3667	Approved
0.7556	Intermediate Similarity	NPD4221	Approved
0.7553	Intermediate Similarity	NPD4753	Phase 2
0.7551	Intermediate Similarity	NPD4755	Approved
0.7551	Intermediate Similarity	NPD5173	Approved
0.7528	Intermediate Similarity	NPD4695	Discontinued
0.7525	Intermediate Similarity	NPD5175	Approved
0.7525	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7449	Intermediate Similarity	NPD4697	Phase 3
0.7429	Intermediate Similarity	NPD4634	Approved
0.7419	Intermediate Similarity	NPD5690	Phase 2
0.74	Intermediate Similarity	NPD4700	Approved
0.7391	Intermediate Similarity	NPD4786	Approved
0.7391	Intermediate Similarity	NPD4197	Approved
0.7374	Intermediate Similarity	NPD7902	Approved
0.734	Intermediate Similarity	NPD3573	Approved
0.7312	Intermediate Similarity	NPD5329	Approved
0.7312	Intermediate Similarity	NPD1694	Approved
0.7308	Intermediate Similarity	NPD5697	Approved
0.7303	Intermediate Similarity	NPD3617	Approved
0.7245	Intermediate Similarity	NPD7748	Approved
0.7238	Intermediate Similarity	NPD4729	Approved
0.7238	Intermediate Similarity	NPD6881	Approved
0.7238	Intermediate Similarity	NPD6011	Approved
0.7238	Intermediate Similarity	NPD4730	Approved
0.7238	Intermediate Similarity	NPD6899	Approved
0.7234	Intermediate Similarity	NPD4689	Approved
0.7234	Intermediate Similarity	NPD5205	Approved
0.7234	Intermediate Similarity	NPD5279	Phase 3
0.7234	Intermediate Similarity	NPD4693	Phase 3
0.7234	Intermediate Similarity	NPD4690	Approved
0.7234	Intermediate Similarity	NPD4688	Approved
0.7234	Intermediate Similarity	NPD4138	Approved
0.7222	Intermediate Similarity	NPD4195	Approved
0.7216	Intermediate Similarity	NPD5281	Approved
0.7216	Intermediate Similarity	NPD5284	Approved
0.7196	Intermediate Similarity	NPD6649	Approved
0.7196	Intermediate Similarity	NPD6650	Approved
0.7184	Intermediate Similarity	NPD4754	Approved
0.717	Intermediate Similarity	NPD6013	Approved
0.717	Intermediate Similarity	NPD6012	Approved
0.717	Intermediate Similarity	NPD6014	Approved
0.7129	Intermediate Similarity	NPD4225	Approved
0.7128	Intermediate Similarity	NPD1696	Phase 3
0.7103	Intermediate Similarity	NPD5251	Approved
0.7103	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5247	Approved
0.7103	Intermediate Similarity	NPD5135	Approved
0.7103	Intermediate Similarity	NPD6883	Approved
0.7103	Intermediate Similarity	NPD5248	Approved
0.7103	Intermediate Similarity	NPD5250	Approved
0.7103	Intermediate Similarity	NPD7290	Approved
0.7103	Intermediate Similarity	NPD5249	Phase 3
0.7103	Intermediate Similarity	NPD7102	Approved
0.7103	Intermediate Similarity	NPD5169	Approved
0.7097	Intermediate Similarity	NPD4788	Approved
0.7075	Intermediate Similarity	NPD5128	Approved
0.7071	Intermediate Similarity	NPD7900	Approved
0.7071	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5280	Approved
0.7053	Intermediate Similarity	NPD4694	Approved
0.7048	Intermediate Similarity	NPD6675	Approved
0.7048	Intermediate Similarity	NPD4768	Approved
0.7048	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD7128	Approved
0.7048	Intermediate Similarity	NPD5739	Approved
0.7048	Intermediate Similarity	NPD4767	Approved
0.7037	Intermediate Similarity	NPD6869	Approved
0.7037	Intermediate Similarity	NPD5215	Approved
0.7037	Intermediate Similarity	NPD5127	Approved
0.7037	Intermediate Similarity	NPD8130	Phase 1
0.7037	Intermediate Similarity	NPD6847	Approved
0.7037	Intermediate Similarity	NPD5217	Approved
0.7037	Intermediate Similarity	NPD6617	Approved
0.7037	Intermediate Similarity	NPD5216	Approved
0.703	Intermediate Similarity	NPD6084	Phase 2
0.703	Intermediate Similarity	NPD6083	Phase 2
0.7009	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6373	Approved
0.6981	Remote Similarity	NPD5701	Approved
0.6972	Remote Similarity	NPD8297	Approved
0.6972	Remote Similarity	NPD6882	Approved
0.697	Remote Similarity	NPD6399	Phase 3
0.6961	Remote Similarity	NPD5696	Approved
0.6947	Remote Similarity	NPD5363	Approved
0.6939	Remote Similarity	NPD5785	Approved
0.6916	Remote Similarity	NPD7320	Approved
0.6916	Remote Similarity	NPD5168	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.6897	Remote Similarity	NPD4691	Approved
0.6893	Remote Similarity	NPD7640	Approved
0.6893	Remote Similarity	NPD7639	Approved
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.6854	Remote Similarity	NPD4058	Approved
0.6847	Remote Similarity	NPD5167	Approved
0.6842	Remote Similarity	NPD3668	Phase 3
0.6842	Remote Similarity	NPD6319	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6837	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5695	Phase 3
0.6809	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7638	Approved
0.6783	Remote Similarity	NPD6015	Approved
0.6783	Remote Similarity	NPD6016	Approved
0.6782	Remote Similarity	NPD4137	Phase 3
0.6774	Remote Similarity	NPD7525	Registered
0.6762	Remote Similarity	NPD5091	Approved
0.6759	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5737	Approved
0.6735	Remote Similarity	NPD6903	Approved
0.6735	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6672	Approved
0.6733	Remote Similarity	NPD6001	Approved
0.6727	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6009	Approved
0.6726	Remote Similarity	NPD6317	Approved
0.6724	Remote Similarity	NPD5988	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.6705	Remote Similarity	NPD4747	Approved
0.6702	Remote Similarity	NPD4139	Approved
0.6702	Remote Similarity	NPD4692	Approved
0.67	Remote Similarity	NPD6411	Approved
0.6697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6313	Approved
0.6638	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6274	Approved
0.6636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5290	Discontinued
0.6634	Remote Similarity	NPD5779	Approved
0.6634	Remote Similarity	NPD5133	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6632	Remote Similarity	NPD4270	Approved
0.6632	Remote Similarity	NPD4269	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6609	Remote Similarity	NPD4522	Approved
0.6609	Remote Similarity	NPD7101	Approved
0.6609	Remote Similarity	NPD7100	Approved
0.6602	Remote Similarity	NPD7614	Phase 1
0.66	Remote Similarity	NPD5207	Approved
0.66	Remote Similarity	NPD4096	Approved
0.6598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6008	Approved
0.6569	Remote Similarity	NPD5282	Discontinued
0.6566	Remote Similarity	NPD5208	Approved
0.6566	Remote Similarity	NPD4518	Approved
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6616	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6535	Remote Similarity	NPD5693	Phase 1
0.6522	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6412	Phase 2
0.6512	Remote Similarity	NPD7341	Phase 2
0.6512	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD6904	Approved
0.6496	Remote Similarity	NPD5983	Phase 2

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