NPASS Compound

Structure

CID156252 OpenBabel06191715522D 29 32 0 0 1 0 0 0 0 0999 V2000 5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 6 0 0 0 12 24 2 0 0 0 0 12 29 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 6 0 0 0 15 20 1 1 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 1 0 0 0 17 20 1 0 0 0 0 17 25 2 0 0 0 0 18 22 1 1 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 20 27 1 1 0 0 0 21 28 1 6 0 0 0 22 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.2
Volume:	405.828
LogP:	1.575
LogD:	0.944
LogS:	-3.395
# Rotatable Bonds:	3
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	5.122
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166
MDCK Permeability:	8.42670415295288e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.861
Human Intestinal Absorption (HIA):	0.648
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	30.338825225830078%
Volume Distribution (VD):	0.701
Pgp-substrate:	62.62993240356445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	1.642
Half-life (T1/2):	0.665

ADMET: Toxicity

hERG Blockers:	0.203
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.921
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.493
Carcinogencity:	0.167
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC156252

Natural Product ID:	NPC156252
*Common Name:**	SDSVJYOOAPRSDA-RPCQODIISA-N
IUPAC Name:	n.a.
Synonyms:	13-Acetylphorbol
Standard InCHIKey:	SDSVJYOOAPRSDA-RPCQODIISA-N
Standard InCHI:	InChI=1S/C22H30O7/c1-10-6-15-20(27,17(10)25)8-13(9-23)7-14-16-19(4,5)22(16,29-12(3)24)18(26)11(2)21(14,15)28/h6-7,11,14-16,18,23,26-28H,8-9H2,1-5H3/t11-,14+,15-,16-,18-,20-,21-,22-/m1/s1
SMILES:	CC1=C[C@@H]2[C@](CC(=C[C@H]3[C@@H]4C(C)(C)[C@@]4([C@@H]([C@@H](C)[C@]23O)O)OC(=O)C)CO)(C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1235429
PubChem CID:	499953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*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	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
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]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	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]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	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
EC50	3
MIC	1
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	101000.0	nM	PMID[553342]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	174000.0	nM	PMID[553342]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1.0	n.a.	PMID[553342]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	217000.0	nM	PMID[553342]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	2.0	n.a.	PMID[553342]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	400.0	ug.mL-1	PMID[553343]

☑ 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 NPC156252 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	241
0.1-0.2	1447
0.2-0.3	4408
0.3-0.4	7260
0.4-0.5	13687
0.5-0.6	8119
0.6-0.7	5970
0.7-0.8	1392
0.8-0.85	49
0.85-0.9	40
0.9-0.95	50
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9725	High Similarity	NPC471125
0.9725	High Similarity	NPC171905
0.9725	High Similarity	NPC472397
0.9725	High Similarity	NPC472758
0.9636	High Similarity	NPC255081
0.9636	High Similarity	NPC471108
0.9636	High Similarity	NPC5989
0.9636	High Similarity	NPC22628
0.9636	High Similarity	NPC275696
0.9636	High Similarity	NPC5991
0.963	High Similarity	NPC472400
0.955	High Similarity	NPC145182
0.955	High Similarity	NPC471128
0.955	High Similarity	NPC157252
0.955	High Similarity	NPC471126
0.9537	High Similarity	NPC472757
0.9464	High Similarity	NPC472401
0.9464	High Similarity	NPC52839
0.9439	High Similarity	NPC153036
0.9381	High Similarity	NPC257017
0.9381	High Similarity	NPC162009
0.9381	High Similarity	NPC19464
0.9364	High Similarity	NPC471127
0.9364	High Similarity	NPC154363
0.9364	High Similarity	NPC234858
0.9352	High Similarity	NPC475937
0.9352	High Similarity	NPC158523
0.9346	High Similarity	NPC163004
0.9298	High Similarity	NPC472399
0.9279	High Similarity	NPC10721
0.9217	High Similarity	NPC145238
0.9204	High Similarity	NPC475885
0.9196	High Similarity	NPC124676
0.9196	High Similarity	NPC146280
0.9182	High Similarity	NPC71889
0.9115	High Similarity	NPC156745
0.9115	High Similarity	NPC236918
0.9099	High Similarity	NPC474872
0.9035	High Similarity	NPC329080
0.9035	High Similarity	NPC472759
0.9	High Similarity	NPC174471
0.9	High Similarity	NPC474871
0.9	High Similarity	NPC96739
0.9	High Similarity	NPC260786
0.8983	High Similarity	NPC270109
0.8938	High Similarity	NPC153651
0.8919	High Similarity	NPC215643
0.8919	High Similarity	NPC170212
0.8919	High Similarity	NPC17138
0.8919	High Similarity	NPC221511
0.8919	High Similarity	NPC265499
0.8919	High Similarity	NPC475391
0.8919	High Similarity	NPC101825
0.8919	High Similarity	NPC89227
0.8919	High Similarity	NPC151216
0.887	High Similarity	NPC185876
0.887	High Similarity	NPC19336
0.886	High Similarity	NPC472760
0.8839	High Similarity	NPC474937
0.8839	High Similarity	NPC477091
0.8814	High Similarity	NPC222307
0.8783	High Similarity	NPC180640
0.8729	High Similarity	NPC473919
0.8729	High Similarity	NPC473709
0.8684	High Similarity	NPC179626
0.8644	High Similarity	NPC473802
0.8583	High Similarity	NPC471940
0.8512	High Similarity	NPC236999
0.85	High Similarity	NPC471939
0.848	Intermediate Similarity	NPC243902
0.8421	Intermediate Similarity	NPC472002
0.8403	Intermediate Similarity	NPC222688
0.8376	Intermediate Similarity	NPC251310
0.8306	Intermediate Similarity	NPC189393
0.8306	Intermediate Similarity	NPC90814
0.8305	Intermediate Similarity	NPC472667
0.8261	Intermediate Similarity	NPC474516
0.8246	Intermediate Similarity	NPC5103
0.824	Intermediate Similarity	NPC476111
0.8235	Intermediate Similarity	NPC143755
0.823	Intermediate Similarity	NPC29827
0.819	Intermediate Similarity	NPC49451
0.816	Intermediate Similarity	NPC475139
0.816	Intermediate Similarity	NPC180902
0.8158	Intermediate Similarity	NPC273433
0.8158	Intermediate Similarity	NPC141350
0.8142	Intermediate Similarity	NPC187435
0.8142	Intermediate Similarity	NPC3316
0.8142	Intermediate Similarity	NPC67321
0.8142	Intermediate Similarity	NPC144854
0.8136	Intermediate Similarity	NPC287343
0.8136	Intermediate Similarity	NPC176513
0.8136	Intermediate Similarity	NPC97908
0.8136	Intermediate Similarity	NPC470775
0.8136	Intermediate Similarity	NPC122033
0.8136	Intermediate Similarity	NPC474654
0.8136	Intermediate Similarity	NPC470854
0.8087	Intermediate Similarity	NPC257240
0.8083	Intermediate Similarity	NPC472004
0.8083	Intermediate Similarity	NPC112038
0.807	Intermediate Similarity	NPC192813
0.807	Intermediate Similarity	NPC154608
0.807	Intermediate Similarity	NPC277017
0.8051	Intermediate Similarity	NPC328374
0.8051	Intermediate Similarity	NPC207217
0.8051	Intermediate Similarity	NPC96312
0.8051	Intermediate Similarity	NPC251236
0.8051	Intermediate Similarity	NPC474734
0.8051	Intermediate Similarity	NPC40632
0.8049	Intermediate Similarity	NPC217901
0.8049	Intermediate Similarity	NPC293112
0.8049	Intermediate Similarity	NPC225049
0.8034	Intermediate Similarity	NPC51978
0.8034	Intermediate Similarity	NPC474271
0.8034	Intermediate Similarity	NPC477126
0.8034	Intermediate Similarity	NPC469454
0.8034	Intermediate Similarity	NPC317210
0.8034	Intermediate Similarity	NPC7921
0.8034	Intermediate Similarity	NPC108721
0.8034	Intermediate Similarity	NPC194100
0.8034	Intermediate Similarity	NPC250109
0.8034	Intermediate Similarity	NPC208998
0.8034	Intermediate Similarity	NPC962
0.8034	Intermediate Similarity	NPC469463
0.8034	Intermediate Similarity	NPC469496
0.8034	Intermediate Similarity	NPC73300
0.8031	Intermediate Similarity	NPC473548
0.8031	Intermediate Similarity	NPC223356
0.8031	Intermediate Similarity	NPC471136
0.8031	Intermediate Similarity	NPC475500
0.8031	Intermediate Similarity	NPC100017
0.8031	Intermediate Similarity	NPC182266
0.8031	Intermediate Similarity	NPC475154
0.8031	Intermediate Similarity	NPC471137
0.8031	Intermediate Similarity	NPC476823
0.8017	Intermediate Similarity	NPC469655
0.8017	Intermediate Similarity	NPC477046
0.8017	Intermediate Similarity	NPC304180
0.8017	Intermediate Similarity	NPC146945
0.8017	Intermediate Similarity	NPC474846
0.8017	Intermediate Similarity	NPC171888
0.8017	Intermediate Similarity	NPC179798
0.8017	Intermediate Similarity	NPC188738
0.8017	Intermediate Similarity	NPC317107
0.8017	Intermediate Similarity	NPC469656
0.8017	Intermediate Similarity	NPC310511
0.8017	Intermediate Similarity	NPC102822
0.8	Intermediate Similarity	NPC475041
0.8	Intermediate Similarity	NPC162495
0.7984	Intermediate Similarity	NPC475273
0.7984	Intermediate Similarity	NPC168849
0.7984	Intermediate Similarity	NPC470882
0.7984	Intermediate Similarity	NPC473253
0.7983	Intermediate Similarity	NPC27999
0.7983	Intermediate Similarity	NPC469684
0.7983	Intermediate Similarity	NPC471854
0.7983	Intermediate Similarity	NPC477116
0.7982	Intermediate Similarity	NPC230541
0.7967	Intermediate Similarity	NPC81736
0.7967	Intermediate Similarity	NPC172154
0.7967	Intermediate Similarity	NPC24651
0.7966	Intermediate Similarity	NPC473798
0.7966	Intermediate Similarity	NPC117712
0.7966	Intermediate Similarity	NPC178289
0.7965	Intermediate Similarity	NPC258532
0.7953	Intermediate Similarity	NPC469673
0.7949	Intermediate Similarity	NPC317687
0.7949	Intermediate Similarity	NPC234042
0.7949	Intermediate Similarity	NPC152117
0.7946	Intermediate Similarity	NPC39996
0.7937	Intermediate Similarity	NPC475606
0.7937	Intermediate Similarity	NPC477189
0.7937	Intermediate Similarity	NPC196921
0.7937	Intermediate Similarity	NPC475314
0.7937	Intermediate Similarity	NPC220757
0.7937	Intermediate Similarity	NPC251564
0.7934	Intermediate Similarity	NPC109973
0.7931	Intermediate Similarity	NPC210005
0.7931	Intermediate Similarity	NPC253906
0.7931	Intermediate Similarity	NPC477103
0.7928	Intermediate Similarity	NPC470074
0.792	Intermediate Similarity	NPC470850
0.7917	Intermediate Similarity	NPC204552
0.7917	Intermediate Similarity	NPC17772
0.7917	Intermediate Similarity	NPC188667
0.7917	Intermediate Similarity	NPC470776
0.7913	Intermediate Similarity	NPC293850
0.7913	Intermediate Similarity	NPC306265
0.7907	Intermediate Similarity	NPC68282
0.7903	Intermediate Similarity	NPC15095
0.7899	Intermediate Similarity	NPC471816
0.7899	Intermediate Similarity	NPC49492
0.7899	Intermediate Similarity	NPC266728
0.7899	Intermediate Similarity	NPC270478
0.7899	Intermediate Similarity	NPC176840
0.7899	Intermediate Similarity	NPC470793
0.7895	Intermediate Similarity	NPC60315
0.7895	Intermediate Similarity	NPC102352
0.7886	Intermediate Similarity	NPC469789
0.7886	Intermediate Similarity	NPC11895

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 NPC156252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1905
0.2-0.3	3651
0.3-0.4	2174
0.4-0.5	789
0.5-0.6	248
0.6-0.7	159
0.7-0.8	14
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
0.8087	Intermediate Similarity	NPD6371	Approved
0.7731	Intermediate Similarity	NPD4632	Approved
0.7692	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6319	Approved
0.7544	Intermediate Similarity	NPD5344	Discontinued
0.7541	Intermediate Similarity	NPD7115	Discovery
0.7521	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7479	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7604	Phase 2
0.7458	Intermediate Similarity	NPD6899	Approved
0.7458	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6881	Approved
0.7436	Intermediate Similarity	NPD6402	Approved
0.7436	Intermediate Similarity	NPD5739	Approved
0.7436	Intermediate Similarity	NPD6675	Approved
0.7436	Intermediate Similarity	NPD7128	Approved
0.7417	Intermediate Similarity	NPD6650	Approved
0.7417	Intermediate Similarity	NPD6649	Approved
0.7398	Intermediate Similarity	NPD6009	Approved
0.7395	Intermediate Similarity	NPD6373	Approved
0.7395	Intermediate Similarity	NPD6012	Approved
0.7395	Intermediate Similarity	NPD6014	Approved
0.7395	Intermediate Similarity	NPD6372	Approved
0.7395	Intermediate Similarity	NPD6013	Approved
0.7373	Intermediate Similarity	NPD5701	Approved
0.7368	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7328	Intermediate Similarity	NPD5211	Phase 2
0.7311	Intermediate Similarity	NPD6011	Approved
0.7311	Intermediate Similarity	NPD7320	Approved
0.7302	Intermediate Similarity	NPD5983	Phase 2
0.7288	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD6847	Approved
0.7273	Intermediate Similarity	NPD8130	Phase 1
0.7266	Intermediate Similarity	NPD7492	Approved
0.7227	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6054	Approved
0.7213	Intermediate Similarity	NPD6882	Approved
0.7209	Intermediate Similarity	NPD6616	Approved
0.7203	Intermediate Similarity	NPD5141	Approved
0.719	Intermediate Similarity	NPD4634	Approved
0.7165	Intermediate Similarity	NPD6016	Approved
0.7165	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD6648	Approved
0.7155	Intermediate Similarity	NPD5285	Approved
0.7155	Intermediate Similarity	NPD4696	Approved
0.7155	Intermediate Similarity	NPD7640	Approved
0.7155	Intermediate Similarity	NPD5286	Approved
0.7155	Intermediate Similarity	NPD7639	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.713	Intermediate Similarity	NPD4755	Approved
0.7109	Intermediate Similarity	NPD6370	Approved
0.7109	Intermediate Similarity	NPD5988	Approved
0.7099	Intermediate Similarity	NPD7736	Approved
0.7087	Intermediate Similarity	NPD6059	Approved
0.7077	Intermediate Similarity	NPD6336	Discontinued
0.7077	Intermediate Similarity	NPD7507	Approved
0.7069	Intermediate Similarity	NPD7638	Approved
0.7045	Intermediate Similarity	NPD7319	Approved
0.704	Intermediate Similarity	NPD6274	Approved
0.7034	Intermediate Similarity	NPD4633	Approved
0.7034	Intermediate Similarity	NPD5224	Approved
0.7034	Intermediate Similarity	NPD5226	Approved
0.7034	Intermediate Similarity	NPD5225	Approved
0.7025	Intermediate Similarity	NPD6686	Approved
0.7023	Intermediate Similarity	NPD8293	Discontinued
0.7009	Intermediate Similarity	NPD4700	Approved
0.7008	Intermediate Similarity	NPD7516	Approved
0.6992	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6083	Phase 2
0.6983	Remote Similarity	NPD6084	Phase 2
0.6975	Remote Similarity	NPD5174	Approved
0.6975	Remote Similarity	NPD5175	Approved
0.6957	Remote Similarity	NPD5695	Phase 3
0.6949	Remote Similarity	NPD5223	Approved
0.6929	Remote Similarity	NPD7327	Approved
0.6929	Remote Similarity	NPD7328	Approved
0.6923	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD8328	Phase 3
0.6909	Remote Similarity	NPD1696	Phase 3
0.6903	Remote Similarity	NPD6698	Approved
0.6903	Remote Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD7100	Approved
0.6875	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD5282	Discontinued
0.685	Remote Similarity	NPD6317	Approved
0.681	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6412	Phase 2
0.68	Remote Similarity	NPD6053	Discontinued
0.6797	Remote Similarity	NPD6313	Approved
0.6797	Remote Similarity	NPD6335	Approved
0.6797	Remote Similarity	NPD6314	Approved
0.6783	Remote Similarity	NPD6399	Phase 3
0.6769	Remote Similarity	NPD6921	Approved
0.6769	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5221	Approved
0.6752	Remote Similarity	NPD5222	Approved
0.6752	Remote Similarity	NPD4697	Phase 3
0.6748	Remote Similarity	NPD4730	Approved
0.6748	Remote Similarity	NPD5128	Approved
0.6748	Remote Similarity	NPD4729	Approved
0.6721	Remote Similarity	NPD4768	Approved
0.6721	Remote Similarity	NPD4767	Approved
0.6695	Remote Similarity	NPD5173	Approved
0.6695	Remote Similarity	NPD7902	Approved
0.6694	Remote Similarity	NPD4754	Approved
0.6694	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5210	Approved
0.6641	Remote Similarity	NPD6909	Approved
0.6641	Remote Similarity	NPD8379	Approved
0.6641	Remote Similarity	NPD8378	Approved
0.6641	Remote Similarity	NPD6908	Approved
0.6641	Remote Similarity	NPD8296	Approved
0.6641	Remote Similarity	NPD8033	Approved
0.6641	Remote Similarity	NPD8380	Approved
0.6641	Remote Similarity	NPD8335	Approved
0.664	Remote Similarity	NPD5248	Approved
0.664	Remote Similarity	NPD5251	Approved
0.664	Remote Similarity	NPD5249	Phase 3
0.664	Remote Similarity	NPD5247	Approved
0.664	Remote Similarity	NPD5250	Approved
0.6638	Remote Similarity	NPD4202	Approved
0.6612	Remote Similarity	NPD7632	Discontinued
0.6593	Remote Similarity	NPD6033	Approved
0.6589	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5217	Approved
0.6587	Remote Similarity	NPD5216	Approved
0.6587	Remote Similarity	NPD5215	Approved
0.6581	Remote Similarity	NPD7748	Approved
0.6565	Remote Similarity	NPD8294	Approved
0.6565	Remote Similarity	NPD8377	Approved
0.6552	Remote Similarity	NPD7983	Approved
0.6552	Remote Similarity	NPD7515	Phase 2
0.6552	Remote Similarity	NPD6079	Approved
0.6549	Remote Similarity	NPD3618	Phase 1
0.6522	Remote Similarity	NPD5328	Approved
0.6515	Remote Similarity	NPD7503	Approved
0.6512	Remote Similarity	NPD6868	Approved
0.6508	Remote Similarity	NPD5169	Approved
0.6508	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5135	Approved
0.6496	Remote Similarity	NPD5778	Approved
0.6496	Remote Similarity	NPD5779	Approved
0.6491	Remote Similarity	NPD7524	Approved
0.6484	Remote Similarity	NPD8133	Approved
0.6466	Remote Similarity	NPD5785	Approved
0.6466	Remote Similarity	NPD7838	Discovery
0.646	Remote Similarity	NPD1694	Approved
0.6457	Remote Similarity	NPD5127	Approved
0.6457	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7260	Phase 2
0.6441	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7900	Approved
0.6441	Remote Similarity	NPD6001	Approved
0.6435	Remote Similarity	NPD5737	Approved
0.6435	Remote Similarity	NPD6672	Approved
0.6429	Remote Similarity	NPD6110	Phase 1
0.641	Remote Similarity	NPD7637	Suspended
0.641	Remote Similarity	NPD5284	Approved
0.641	Remote Similarity	NPD5693	Phase 1
0.641	Remote Similarity	NPD5281	Approved
0.6391	Remote Similarity	NPD8517	Approved
0.6391	Remote Similarity	NPD8513	Phase 3
0.6391	Remote Similarity	NPD8515	Approved
0.6391	Remote Similarity	NPD8516	Approved
0.6379	Remote Similarity	NPD6080	Approved
0.6379	Remote Similarity	NPD6904	Approved
0.6379	Remote Similarity	NPD6673	Approved
0.6348	Remote Similarity	NPD3573	Approved
0.6339	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5692	Phase 3
0.6316	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5363	Approved
0.6308	Remote Similarity	NPD5167	Approved
0.6283	Remote Similarity	NPD7154	Phase 3
0.6283	Remote Similarity	NPD5362	Discontinued
0.6271	Remote Similarity	NPD8034	Phase 2
0.6271	Remote Similarity	NPD8035	Phase 2
0.6271	Remote Similarity	NPD6050	Approved
0.6271	Remote Similarity	NPD5694	Approved
0.6261	Remote Similarity	NPD7334	Approved
0.6261	Remote Similarity	NPD7146	Approved
0.6261	Remote Similarity	NPD5279	Phase 3
0.6261	Remote Similarity	NPD5330	Approved
0.6261	Remote Similarity	NPD7521	Approved
0.6261	Remote Similarity	NPD6684	Approved
0.6261	Remote Similarity	NPD6409	Approved
0.6261	Remote Similarity	NPD5690	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