NPASS Compound

Structure

CID311781 OpenBabel06191716122D 27 31 0 0 1 0 0 0 0 0999 V2000 1.2322 3.0379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5133 -2.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1758 -1.6572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2217 1.7269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2218 -1.7273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4738 2.1587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4738 -2.1591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2218 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7176 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9697 0.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3733 2.9477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7341 -1.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2218 0.8632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2218 -0.8636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9697 -0.4318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7259 1.7269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7259 -1.7273 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4738 0.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7259 0.8632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7259 -0.8637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4738 -0.4318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7176 -0.8636 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1343 3.6464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6668 -0.8094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0220 2.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0220 -2.1591 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 11 1 0 0 0 0 2 12 1 0 0 0 0 3 22 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 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 9 22 1 0 0 0 0 10 13 1 0 0 0 0 11 23 2 0 0 0 0 11 25 1 0 0 0 0 12 24 2 0 0 0 0 12 26 1 0 0 0 0 13 18 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 1 0 0 0 15 10 1 6 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 1 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 1 0 0 0 20 27 1 0 0 0 0 21 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.16
Volume:	368.119
LogP:	1.984
LogD:	1.105
LogS:	-3.892
# Rotatable Bonds:	4
TPSA:	65.07
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	5.27
Fsp3:	0.524
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:	-5.022
MDCK Permeability:	3.164048757753335e-05
Pgp-inhibitor:	0.55
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	14.10765266418457%
Volume Distribution (VD):	0.807
Pgp-substrate:	74.15287780761719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.5
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.771

ADMET: Excretion

Clearance (CL):	2.639
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.492
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.573
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.648
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC311781

Natural Product ID:	NPC311781
*Common Name:**	Diacetylmorphine
IUPAC Name:	[(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl] acetate
Synonyms:
Standard InCHIKey:	GVGLGOZIDCSQPN-PVHGPHFFSA-N
Standard InCHI:	InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
SMILES:	CC(=O)Oc1ccc2C[C@@H]3[C@@H]4C=C[C@@H]([C@H]5[C@]4(CCN3C)c2c1O5)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459324
PubChem CID:	5462328
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000058] Morphinans

*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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	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
Others	8
Potency	2

Activity Type	# Activity
Individual Protein	2
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Km	=	6300000.0	nM	PMID[509505]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	pKm	=	2.2	n.a.	PMID[509505]
NPT35	Others	n.a.		pKa	=	7.95	n.a.	PMID[509503]
NPT35	Others	n.a.		LogD	=	0.85	n.a.	PMID[509503]
NPT35	Others	n.a.		LogD	=	-0.94	n.a.	PMID[509503]
NPT35	Others	n.a.		LogD	=	1.58	n.a.	PMID[509503]
NPT35	Others	n.a.		LogP	=	1.5	n.a.	PMID[509504]
NPT35	Others	n.a.		pKa	n.a.	7.96	n.a.	PMID[509506]
NPT2	Others	Unspecified		Potency	n.a.	26603.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	375.8	nM	PubChem BioAssay data set

☑ 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 NPC311781 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	274
0.1-0.2	1330
0.2-0.3	3738
0.3-0.4	11100
0.4-0.5	7780
0.5-0.6	11825
0.6-0.7	5825
0.7-0.8	738
0.8-0.85	64
0.85-0.9	16
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9719	High Similarity	NPC174783
0.9402	High Similarity	NPC140577
0.9402	High Similarity	NPC43069
0.9297	High Similarity	NPC67346
0.9194	High Similarity	NPC232533
0.9101	High Similarity	NPC157958
0.9091	High Similarity	NPC243483
0.9091	High Similarity	NPC97086
0.9006	High Similarity	NPC214629
0.8848	High Similarity	NPC126211
0.8736	High Similarity	NPC115906
0.827	Intermediate Similarity	NPC35680
0.8238	Intermediate Similarity	NPC66909
0.8138	Intermediate Similarity	NPC298339
0.8011	Intermediate Similarity	NPC227683
0.798	Intermediate Similarity	NPC151470
0.798	Intermediate Similarity	NPC201055
0.798	Intermediate Similarity	NPC64576
0.798	Intermediate Similarity	NPC254045
0.7969	Intermediate Similarity	NPC162694
0.7967	Intermediate Similarity	NPC475780
0.7927	Intermediate Similarity	NPC141440
0.7846	Intermediate Similarity	NPC196231
0.7822	Intermediate Similarity	NPC476500
0.7817	Intermediate Similarity	NPC33256
0.7802	Intermediate Similarity	NPC323443
0.7802	Intermediate Similarity	NPC180756
0.7761	Intermediate Similarity	NPC244191
0.7688	Intermediate Similarity	NPC279665
0.7626	Intermediate Similarity	NPC94499
0.7582	Intermediate Similarity	NPC8337
0.7582	Intermediate Similarity	NPC85747
0.7577	Intermediate Similarity	NPC305847
0.7574	Intermediate Similarity	NPC474427
0.7566	Intermediate Similarity	NPC284842
0.7562	Intermediate Similarity	NPC293624
0.7561	Intermediate Similarity	NPC80472
0.7538	Intermediate Similarity	NPC302449
0.7526	Intermediate Similarity	NPC27887
0.7526	Intermediate Similarity	NPC149285
0.7513	Intermediate Similarity	NPC124657
0.7512	Intermediate Similarity	NPC475713
0.7512	Intermediate Similarity	NPC474432
0.7487	Intermediate Similarity	NPC63152
0.7475	Intermediate Similarity	NPC46744
0.7475	Intermediate Similarity	NPC73020
0.7475	Intermediate Similarity	NPC14622
0.7475	Intermediate Similarity	NPC124302
0.7475	Intermediate Similarity	NPC70290
0.7475	Intermediate Similarity	NPC215098
0.7463	Intermediate Similarity	NPC477258
0.746	Intermediate Similarity	NPC255607
0.746	Intermediate Similarity	NPC3375
0.744	Intermediate Similarity	NPC326895
0.7415	Intermediate Similarity	NPC286135
0.7407	Intermediate Similarity	NPC476569
0.7404	Intermediate Similarity	NPC94687
0.7404	Intermediate Similarity	NPC106840
0.7404	Intermediate Similarity	NPC476495
0.7402	Intermediate Similarity	NPC72788
0.7402	Intermediate Similarity	NPC314100
0.7402	Intermediate Similarity	NPC226652
0.7402	Intermediate Similarity	NPC120671
0.7396	Intermediate Similarity	NPC474708
0.7396	Intermediate Similarity	NPC298071
0.7389	Intermediate Similarity	NPC83019
0.7368	Intermediate Similarity	NPC46990
0.7347	Intermediate Similarity	NPC220961
0.7344	Intermediate Similarity	NPC475845
0.734	Intermediate Similarity	NPC204580
0.7333	Intermediate Similarity	NPC241704
0.733	Intermediate Similarity	NPC202771
0.733	Intermediate Similarity	NPC2173
0.733	Intermediate Similarity	NPC328700
0.733	Intermediate Similarity	NPC119818
0.7326	Intermediate Similarity	NPC476443
0.7326	Intermediate Similarity	NPC133817
0.7302	Intermediate Similarity	NPC26353
0.7302	Intermediate Similarity	NPC226428
0.73	Intermediate Similarity	NPC166979
0.73	Intermediate Similarity	NPC237579
0.7292	Intermediate Similarity	NPC132054
0.7292	Intermediate Similarity	NPC474324
0.7292	Intermediate Similarity	NPC57812
0.7286	Intermediate Similarity	NPC476496
0.7277	Intermediate Similarity	NPC35345
0.7273	Intermediate Similarity	NPC10429
0.7259	Intermediate Similarity	NPC32154
0.7254	Intermediate Similarity	NPC41689
0.7254	Intermediate Similarity	NPC279768
0.725	Intermediate Similarity	NPC230098
0.7246	Intermediate Similarity	NPC475747
0.724	Intermediate Similarity	NPC24264
0.724	Intermediate Similarity	NPC476432
0.7228	Intermediate Similarity	NPC71821
0.7212	Intermediate Similarity	NPC207971
0.7209	Intermediate Similarity	NPC475180
0.7206	Intermediate Similarity	NPC470646
0.7204	Intermediate Similarity	NPC474305
0.7204	Intermediate Similarity	NPC476579
0.7202	Intermediate Similarity	NPC247389
0.7196	Intermediate Similarity	NPC476572
0.7196	Intermediate Similarity	NPC473746
0.7188	Intermediate Similarity	NPC302527
0.7188	Intermediate Similarity	NPC167546
0.7188	Intermediate Similarity	NPC225774
0.7188	Intermediate Similarity	NPC16805
0.7188	Intermediate Similarity	NPC216092
0.7181	Intermediate Similarity	NPC325871
0.7181	Intermediate Similarity	NPC99659
0.7179	Intermediate Similarity	NPC67978
0.7179	Intermediate Similarity	NPC303581
0.7173	Intermediate Similarity	NPC153631
0.7172	Intermediate Similarity	NPC474745
0.7166	Intermediate Similarity	NPC470924
0.7164	Intermediate Similarity	NPC169387
0.7164	Intermediate Similarity	NPC477259
0.7163	Intermediate Similarity	NPC38964
0.7158	Intermediate Similarity	NPC106786
0.7158	Intermediate Similarity	NPC118804
0.7157	Intermediate Similarity	NPC222524
0.7151	Intermediate Similarity	NPC475848
0.7151	Intermediate Similarity	NPC474306
0.715	Intermediate Similarity	NPC219341
0.7143	Intermediate Similarity	NPC329992
0.7143	Intermediate Similarity	NPC256422
0.7143	Intermediate Similarity	NPC226708
0.7135	Intermediate Similarity	NPC243509
0.7135	Intermediate Similarity	NPC59567
0.7129	Intermediate Similarity	NPC208890
0.7121	Intermediate Similarity	NPC477560
0.7121	Intermediate Similarity	NPC474325
0.7113	Intermediate Similarity	NPC308156
0.7113	Intermediate Similarity	NPC210918
0.7111	Intermediate Similarity	NPC160113
0.7111	Intermediate Similarity	NPC476220
0.7107	Intermediate Similarity	NPC308267
0.7107	Intermediate Similarity	NPC304675
0.7104	Intermediate Similarity	NPC27220
0.71	Intermediate Similarity	NPC233718
0.7097	Intermediate Similarity	NPC82056
0.7095	Intermediate Similarity	NPC268077
0.7092	Intermediate Similarity	NPC302392
0.7083	Intermediate Similarity	NPC33320
0.7083	Intermediate Similarity	NPC472299
0.7083	Intermediate Similarity	NPC68619
0.708	Intermediate Similarity	NPC154922
0.7077	Intermediate Similarity	NPC179015
0.7077	Intermediate Similarity	NPC173149
0.7077	Intermediate Similarity	NPC473753
0.7077	Intermediate Similarity	NPC473766
0.7071	Intermediate Similarity	NPC474470
0.7071	Intermediate Similarity	NPC237044
0.7068	Intermediate Similarity	NPC7059
0.7065	Intermediate Similarity	NPC475981
0.7065	Intermediate Similarity	NPC474746
0.7065	Intermediate Similarity	NPC475566
0.7062	Intermediate Similarity	NPC474858
0.7059	Intermediate Similarity	NPC472839
0.7047	Intermediate Similarity	NPC139876
0.7047	Intermediate Similarity	NPC471003
0.7047	Intermediate Similarity	NPC21046
0.7041	Intermediate Similarity	NPC291742
0.7041	Intermediate Similarity	NPC255787
0.7041	Intermediate Similarity	NPC155264
0.7041	Intermediate Similarity	NPC193881
0.7041	Intermediate Similarity	NPC67450
0.7041	Intermediate Similarity	NPC210460
0.7037	Intermediate Similarity	NPC294511
0.7037	Intermediate Similarity	NPC55470
0.7037	Intermediate Similarity	NPC121615
0.7035	Intermediate Similarity	NPC118633
0.7035	Intermediate Similarity	NPC294790
0.7035	Intermediate Similarity	NPC148693
0.7035	Intermediate Similarity	NPC309692
0.7031	Intermediate Similarity	NPC123153
0.7031	Intermediate Similarity	NPC266753
0.7031	Intermediate Similarity	NPC477559
0.7031	Intermediate Similarity	NPC232924
0.7031	Intermediate Similarity	NPC160298
0.7031	Intermediate Similarity	NPC473368
0.7031	Intermediate Similarity	NPC306902
0.703	Intermediate Similarity	NPC18306
0.7028	Intermediate Similarity	NPC308943
0.7026	Intermediate Similarity	NPC475779
0.7021	Intermediate Similarity	NPC81733
0.7021	Intermediate Similarity	NPC326316
0.7021	Intermediate Similarity	NPC228842
0.702	Intermediate Similarity	NPC51404
0.702	Intermediate Similarity	NPC329969
0.7015	Intermediate Similarity	NPC248642
0.701	Intermediate Similarity	NPC180306
0.701	Intermediate Similarity	NPC14499
0.701	Intermediate Similarity	NPC475039
0.701	Intermediate Similarity	NPC476035
0.7005	Intermediate Similarity	NPC470088
0.7005	Intermediate Similarity	NPC149090
0.7005	Intermediate Similarity	NPC19520
0.7	Intermediate Similarity	NPC126284
0.7	Intermediate Similarity	NPC99179

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 NPC311781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	698
0.2-0.3	1056
0.3-0.4	2419
0.4-0.5	2375
0.5-0.6	1589
0.6-0.7	663
0.7-0.8	134
0.8-0.85	22
0.85-0.9	9
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4482	Phase 3
0.9832	High Similarity	NPD4107	Approved
0.9402	High Similarity	NPD2972	Approved
0.9402	High Similarity	NPD3533	Approved
0.9297	High Similarity	NPD3057	Approved
0.9194	High Similarity	NPD2491	Approved
0.9171	High Similarity	NPD5980	Discovery
0.911	High Similarity	NPD5676	Approved
0.9091	High Similarity	NPD3448	Approved
0.8894	High Similarity	NPD5619	Clinical (unspecified phase)
0.8736	High Similarity	NPD2971	Approved
0.8736	High Similarity	NPD2968	Approved
0.8515	High Similarity	NPD7907	Approved
0.8507	High Similarity	NPD4665	Approved
0.8507	High Similarity	NPD4111	Phase 1
0.8398	Intermediate Similarity	NPD4481	Phase 3
0.836	Intermediate Similarity	NPD2490	Approved
0.836	Intermediate Similarity	NPD2488	Approved
0.8238	Intermediate Similarity	NPD2973	Approved
0.8238	Intermediate Similarity	NPD2974	Approved
0.8238	Intermediate Similarity	NPD2975	Approved
0.8205	Intermediate Similarity	NPD4580	Approved
0.8138	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2494	Approved
0.8071	Intermediate Similarity	NPD2493	Approved
0.804	Intermediate Similarity	NPD4583	Approved
0.804	Intermediate Similarity	NPD4582	Approved
0.8	Intermediate Similarity	NPD7048	Phase 3
0.799	Intermediate Similarity	NPD4004	Approved
0.799	Intermediate Similarity	NPD4002	Approved
0.798	Intermediate Similarity	NPD3452	Approved
0.798	Intermediate Similarity	NPD3450	Approved
0.7861	Intermediate Similarity	NPD4040	Phase 1
0.7754	Intermediate Similarity	NPD2969	Approved
0.7754	Intermediate Similarity	NPD2970	Approved
0.7701	Intermediate Similarity	NPD3051	Approved
0.7619	Intermediate Similarity	NPD27	Approved
0.7619	Intermediate Similarity	NPD2489	Approved
0.7577	Intermediate Similarity	NPD7310	Approved
0.7577	Intermediate Similarity	NPD7312	Approved
0.7577	Intermediate Similarity	NPD7313	Approved
0.7577	Intermediate Similarity	NPD7311	Approved
0.7538	Intermediate Similarity	NPD7309	Approved
0.7488	Intermediate Similarity	NPD7047	Phase 3
0.7475	Intermediate Similarity	NPD4420	Approved
0.7473	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6385	Approved
0.7405	Intermediate Similarity	NPD6386	Approved
0.7379	Intermediate Similarity	NPD7497	Discontinued
0.733	Intermediate Similarity	NPD5005	Approved
0.733	Intermediate Similarity	NPD5006	Approved
0.7291	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6997	Phase 2
0.7222	Intermediate Similarity	NPD4578	Approved
0.7222	Intermediate Similarity	NPD4577	Approved
0.72	Intermediate Similarity	NPD4663	Approved
0.7164	Intermediate Similarity	NPD7906	Approved
0.7143	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5978	Approved
0.7105	Intermediate Similarity	NPD5977	Approved
0.7092	Intermediate Similarity	NPD7177	Discontinued
0.7092	Intermediate Similarity	NPD2163	Approved
0.7092	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD919	Approved
0.7056	Intermediate Similarity	NPD5312	Approved
0.7056	Intermediate Similarity	NPD5313	Approved
0.7043	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6873	Phase 2
0.7035	Intermediate Similarity	NPD7038	Approved
0.7035	Intermediate Similarity	NPD7039	Approved
0.7005	Intermediate Similarity	NPD3641	Approved
0.7005	Intermediate Similarity	NPD3639	Approved
0.7005	Intermediate Similarity	NPD3640	Phase 3
0.6995	Remote Similarity	NPD7291	Discontinued
0.6995	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8404	Phase 2
0.6927	Remote Similarity	NPD5353	Approved
0.6923	Remote Similarity	NPD5564	Approved
0.6915	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD2898	Approved
0.6898	Remote Similarity	NPD3146	Approved
0.6898	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7315	Approved
0.6888	Remote Similarity	NPD6071	Discontinued
0.6884	Remote Similarity	NPD5844	Phase 1
0.6857	Remote Similarity	NPD8285	Discontinued
0.6853	Remote Similarity	NPD5242	Approved
0.6845	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6625	Approved
0.6839	Remote Similarity	NPD2560	Approved
0.6839	Remote Similarity	NPD2563	Approved
0.6837	Remote Similarity	NPD6107	Approved
0.6837	Remote Similarity	NPD4859	Phase 1
0.6825	Remote Similarity	NPD5457	Discontinued
0.6821	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5494	Approved
0.6776	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7110	Phase 1
0.6763	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2897	Discontinued
0.674	Remote Similarity	NPD3142	Approved
0.674	Remote Similarity	NPD3140	Approved
0.6734	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4584	Approved
0.6702	Remote Similarity	NPD4210	Discontinued
0.67	Remote Similarity	NPD3446	Phase 1
0.6667	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7549	Discontinued
0.6651	Remote Similarity	NPD7296	Approved
0.665	Remote Similarity	NPD5709	Phase 3
0.6649	Remote Similarity	NPD4727	Phase 1
0.6649	Remote Similarity	NPD7427	Discontinued
0.6648	Remote Similarity	NPD3109	Approved
0.6648	Remote Similarity	NPD3110	Approved
0.6637	Remote Similarity	NPD7278	Phase 2
0.6637	Remote Similarity	NPD7279	Phase 2
0.6635	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8156	Discontinued
0.6634	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8469	Approved
0.6618	Remote Similarity	NPD8434	Phase 2
0.6616	Remote Similarity	NPD4666	Phase 3
0.6615	Remote Similarity	NPD4585	Approved
0.6614	Remote Similarity	NPD6667	Approved
0.6614	Remote Similarity	NPD6666	Approved
0.6608	Remote Similarity	NPD4505	Phase 1
0.6604	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6618	Phase 2
0.6599	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4773	Phase 2
0.6598	Remote Similarity	NPD5890	Approved
0.6598	Remote Similarity	NPD4772	Phase 2
0.6598	Remote Similarity	NPD5889	Approved
0.6596	Remote Similarity	NPD5754	Discontinued
0.6584	Remote Similarity	NPD8252	Approved
0.6584	Remote Similarity	NPD8099	Discontinued
0.6584	Remote Similarity	NPD8251	Approved
0.6582	Remote Similarity	NPD3817	Phase 2
0.6579	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7248	Discontinued
0.6564	Remote Similarity	NPD7577	Discontinued
0.6562	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4361	Phase 2
0.655	Remote Similarity	NPD5710	Approved
0.655	Remote Similarity	NPD5711	Approved
0.655	Remote Similarity	NPD6808	Phase 2
0.6548	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6876	Approved
0.6546	Remote Similarity	NPD6875	Approved
0.6546	Remote Similarity	NPD6599	Discontinued
0.6545	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.654	Remote Similarity	NPD4466	Phase 1
0.6537	Remote Similarity	NPD6765	Approved
0.6537	Remote Similarity	NPD6764	Approved
0.6531	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.653	Remote Similarity	NPD7701	Phase 2
0.6528	Remote Similarity	NPD3687	Approved
0.6528	Remote Similarity	NPD3686	Approved
0.6522	Remote Similarity	NPD6853	Approved
0.6522	Remote Similarity	NPD6851	Approved
0.6515	Remote Similarity	NPD7831	Phase 2
0.6515	Remote Similarity	NPD7833	Phase 2
0.6515	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6273	Approved
0.6509	Remote Similarity	NPD4363	Phase 3
0.6509	Remote Similarity	NPD4360	Phase 2
0.6508	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD4110	Phase 3
0.6508	Remote Similarity	NPD4628	Phase 3
0.649	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5036	Approved
0.6488	Remote Similarity	NPD6297	Approved
0.6486	Remote Similarity	NPD2653	Approved
0.6482	Remote Similarity	NPD6862	Phase 2
0.648	Remote Similarity	NPD6844	Discontinued
0.6477	Remote Similarity	NPD1670	Discontinued
0.6476	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5241	Discontinued
0.6474	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6042	Phase 2
0.6471	Remote Similarity	NPD42	Phase 2
0.6468	Remote Similarity	NPD4166	Phase 2
0.6468	Remote Similarity	NPD8319	Approved
0.6468	Remote Similarity	NPD8320	Phase 1
0.6465	Remote Similarity	NPD1880	Phase 3
0.6465	Remote Similarity	NPD3882	Suspended
0.6462	Remote Similarity	NPD6585	Discontinued
0.6459	Remote Similarity	NPD5037	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