NPASS Compound

Structure

CID283999 OpenBabel06191716092D 25 29 0 0 1 0 0 0 0 0999 V2000 3.4456 -4.0195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7270 0.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3865 0.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8780 0.4989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5082 0.8943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5960 -1.5024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7560 -0.9978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 -2.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0314 -1.9896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1358 -3.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7250 -0.9915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8783 -0.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7111 -3.0112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 -1.4905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5891 -2.5123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7389 -1.9607 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9090 -2.4883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7043 -4.0120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0138 -0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8341 -4.5065 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.5676 -4.5184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4524 -3.0186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4971 -2.5870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1543 -3.4406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 4 1 0 0 0 0 2 11 1 0 0 0 0 3 5 1 0 0 0 0 3 12 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 8 14 2 0 0 0 0 9 19 1 0 0 0 0 10 24 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 23 1 0 0 0 0 16 7 1 1 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 9 1 1 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.16
Volume:	338.37
LogP:	1.542
LogD:	1.539
LogS:	-2.549
# Rotatable Bonds:	2
TPSA:	74.02
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.821
Synthetic Accessibility Score:	4.722
Fsp3:	0.526
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:	-4.888
MDCK Permeability:	9.15854161576135e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.265

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.849
Plasma Protein Binding (PPB):	41.106658935546875%
Volume Distribution (VD):	1.77
Pgp-substrate:	67.18966674804688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.875
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.337
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.898

ADMET: Excretion

Clearance (CL):	9.928
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.187
AMES Toxicity:	0.935
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.041
Carcinogencity:	0.926
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC283999

Natural Product ID:	NPC283999
*Common Name:**	QCGHEAJFTHQMHI-SCTDSRPQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QCGHEAJFTHQMHI-SCTDSRPQSA-N
Standard InCHI:	InChI=1S/C19H22N2O4/c1-23-15-6-11-2-4-21-5-3-12-7-16-17(25-10-24-16)9-19(12,21)14(11)8-13(15)18(20)22/h6-8,16-17H,2-5,9-10H2,1H3,(H2,20,22)/t16-,17+,19-/m0/s1
SMILES:	COc1cc2CCN3[C@@]4(c2cc1C(=N)O)C[C@H]1OCO[C@H]1C=C4CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465625
PubChem CID:	16091679
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001782] Erythrina alkaloids [CHEMONTID:0002780] Erythrinanes

*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
NPO19806	Vismia guineensis	Species	Hypericaceae	Eukaryota	Roots	Mali	1995-JUL	PMID[10650071]
NPO16672	Cucurbita foetidissima	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[10650092]
NPO19604	Hyperbaena valida	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067175]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19604	Hyperbaena valida	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18965	Actinopyga flammea	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16893	Lecidea fuscoatra	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19481	Gynotroches axillaris	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13733	Saccharopolyspora erythraea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4119	Oxyanthus pallidus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16672	Cucurbita foetidissima	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19806	Vismia guineensis	Species	Hypericaceae	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	1

Activity Type	# Activity
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	IC50	=	94000.0	nM	PMID[489566]

☑ 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 NPC283999 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	288
0.1-0.2	1381
0.2-0.3	5186
0.3-0.4	12335
0.4-0.5	8610
0.5-0.6	12538
0.6-0.7	1853
0.7-0.8	493
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8363	Intermediate Similarity	NPC181653
0.8363	Intermediate Similarity	NPC190332
0.8294	Intermediate Similarity	NPC320104
0.8284	Intermediate Similarity	NPC97072
0.8284	Intermediate Similarity	NPC215829
0.8256	Intermediate Similarity	NPC100566
0.8222	Intermediate Similarity	NPC166979
0.8198	Intermediate Similarity	NPC476002
0.8192	Intermediate Similarity	NPC244554
0.8182	Intermediate Similarity	NPC237044
0.8161	Intermediate Similarity	NPC75958
0.8155	Intermediate Similarity	NPC78733
0.8144	Intermediate Similarity	NPC148898
0.8136	Intermediate Similarity	NPC118633
0.8136	Intermediate Similarity	NPC294790
0.8136	Intermediate Similarity	NPC474325
0.8136	Intermediate Similarity	NPC148693
0.8125	Intermediate Similarity	NPC304675
0.8114	Intermediate Similarity	NPC470739
0.8114	Intermediate Similarity	NPC225597
0.8114	Intermediate Similarity	NPC477640
0.8103	Intermediate Similarity	NPC290759
0.8103	Intermediate Similarity	NPC82533
0.8103	Intermediate Similarity	NPC266176
0.8103	Intermediate Similarity	NPC475686
0.8103	Intermediate Similarity	NPC58766
0.8103	Intermediate Similarity	NPC158148
0.809	Intermediate Similarity	NPC474745
0.8057	Intermediate Similarity	NPC474475
0.8057	Intermediate Similarity	NPC311991
0.8056	Intermediate Similarity	NPC475981
0.8056	Intermediate Similarity	NPC474746
0.8046	Intermediate Similarity	NPC298979
0.8046	Intermediate Similarity	NPC474324
0.8046	Intermediate Similarity	NPC57812
0.8023	Intermediate Similarity	NPC187678
0.8012	Intermediate Similarity	NPC477080
0.8011	Intermediate Similarity	NPC9867
0.8	Intermediate Similarity	NPC475845
0.8	Intermediate Similarity	NPC275132
0.7965	Intermediate Similarity	NPC205167
0.7955	Intermediate Similarity	NPC474708
0.7943	Intermediate Similarity	NPC210918
0.7933	Intermediate Similarity	NPC15919
0.7931	Intermediate Similarity	NPC276944
0.7931	Intermediate Similarity	NPC238530
0.7931	Intermediate Similarity	NPC232514
0.7929	Intermediate Similarity	NPC223124
0.7921	Intermediate Similarity	NPC199465
0.7921	Intermediate Similarity	NPC128560
0.7921	Intermediate Similarity	NPC229166
0.7917	Intermediate Similarity	NPC274026
0.791	Intermediate Similarity	NPC65403
0.7903	Intermediate Similarity	NPC162653
0.7901	Intermediate Similarity	NPC248642
0.7895	Intermediate Similarity	NPC234392
0.7895	Intermediate Similarity	NPC31311
0.7889	Intermediate Similarity	NPC126284
0.7877	Intermediate Similarity	NPC474470
0.7869	Intermediate Similarity	NPC57036
0.7869	Intermediate Similarity	NPC230098
0.7869	Intermediate Similarity	NPC214116
0.7865	Intermediate Similarity	NPC2314
0.7861	Intermediate Similarity	NPC266753
0.7861	Intermediate Similarity	NPC477559
0.7861	Intermediate Similarity	NPC232924
0.7861	Intermediate Similarity	NPC160298
0.7861	Intermediate Similarity	NPC306902
0.7861	Intermediate Similarity	NPC4304
0.7861	Intermediate Similarity	NPC249274
0.7857	Intermediate Similarity	NPC156576
0.7853	Intermediate Similarity	NPC152212
0.7845	Intermediate Similarity	NPC312918
0.7845	Intermediate Similarity	NPC476574
0.7845	Intermediate Similarity	NPC477561
0.7845	Intermediate Similarity	NPC155442
0.7836	Intermediate Similarity	NPC138487
0.7836	Intermediate Similarity	NPC216459
0.7836	Intermediate Similarity	NPC41178
0.7833	Intermediate Similarity	NPC320223
0.7833	Intermediate Similarity	NPC114364
0.7829	Intermediate Similarity	NPC16805
0.7829	Intermediate Similarity	NPC302527
0.7829	Intermediate Similarity	NPC167546
0.7829	Intermediate Similarity	NPC231198
0.7829	Intermediate Similarity	NPC180306
0.7826	Intermediate Similarity	NPC476576
0.7826	Intermediate Similarity	NPC186546
0.7824	Intermediate Similarity	NPC233029
0.7824	Intermediate Similarity	NPC210148
0.7824	Intermediate Similarity	NPC82285
0.7824	Intermediate Similarity	NPC133011
0.7811	Intermediate Similarity	NPC223125
0.7809	Intermediate Similarity	NPC149090
0.7809	Intermediate Similarity	NPC19520
0.7803	Intermediate Similarity	NPC111485
0.7798	Intermediate Similarity	NPC475959
0.7796	Intermediate Similarity	NPC117717
0.7791	Intermediate Similarity	NPC147091
0.7791	Intermediate Similarity	NPC146288
0.7784	Intermediate Similarity	NPC304659
0.7784	Intermediate Similarity	NPC86144
0.7784	Intermediate Similarity	NPC476432
0.7784	Intermediate Similarity	NPC24264
0.7771	Intermediate Similarity	NPC233650
0.776	Intermediate Similarity	NPC135772
0.7759	Intermediate Similarity	NPC165797
0.7753	Intermediate Similarity	NPC6152
0.7746	Intermediate Similarity	NPC79328
0.774	Intermediate Similarity	NPC247389
0.7733	Intermediate Similarity	NPC76079
0.7727	Intermediate Similarity	NPC134858
0.7727	Intermediate Similarity	NPC225774
0.7725	Intermediate Similarity	NPC130926
0.7722	Intermediate Similarity	NPC477558
0.7722	Intermediate Similarity	NPC49353
0.7705	Intermediate Similarity	NPC233718
0.7705	Intermediate Similarity	NPC476575
0.7705	Intermediate Similarity	NPC116284
0.7701	Intermediate Similarity	NPC221864
0.7701	Intermediate Similarity	NPC92191
0.7701	Intermediate Similarity	NPC59028
0.7701	Intermediate Similarity	NPC302001
0.7692	Intermediate Similarity	NPC258695
0.7692	Intermediate Similarity	NPC470879
0.7692	Intermediate Similarity	NPC99179
0.7688	Intermediate Similarity	NPC82763
0.7684	Intermediate Similarity	NPC195392
0.7684	Intermediate Similarity	NPC219341
0.767	Intermediate Similarity	NPC189470
0.767	Intermediate Similarity	NPC218614
0.7667	Intermediate Similarity	NPC228040
0.7657	Intermediate Similarity	NPC230956
0.7657	Intermediate Similarity	NPC119649
0.7657	Intermediate Similarity	NPC271388
0.7657	Intermediate Similarity	NPC235143
0.7657	Intermediate Similarity	NPC205255
0.765	Intermediate Similarity	NPC32413
0.765	Intermediate Similarity	NPC474506
0.764	Intermediate Similarity	NPC252960
0.764	Intermediate Similarity	NPC210140
0.764	Intermediate Similarity	NPC150879
0.7637	Intermediate Similarity	NPC23219
0.7633	Intermediate Similarity	NPC476151
0.763	Intermediate Similarity	NPC93593
0.7627	Intermediate Similarity	NPC209377
0.7627	Intermediate Similarity	NPC247972
0.7614	Intermediate Similarity	NPC80759
0.7614	Intermediate Similarity	NPC79402
0.76	Intermediate Similarity	NPC69360
0.7598	Intermediate Similarity	NPC241055
0.7596	Intermediate Similarity	NPC267408
0.7588	Intermediate Similarity	NPC59907
0.7588	Intermediate Similarity	NPC37144
0.7586	Intermediate Similarity	NPC29647
0.7586	Intermediate Similarity	NPC186063
0.7584	Intermediate Similarity	NPC56887
0.7584	Intermediate Similarity	NPC223077
0.7584	Intermediate Similarity	NPC193853
0.7582	Intermediate Similarity	NPC112575
0.7571	Intermediate Similarity	NPC59567
0.7571	Intermediate Similarity	NPC324144
0.7561	Intermediate Similarity	NPC7018
0.7557	Intermediate Similarity	NPC166014
0.7557	Intermediate Similarity	NPC27410
0.7556	Intermediate Similarity	NPC474953
0.7554	Intermediate Similarity	NPC179704
0.7553	Intermediate Similarity	NPC475754
0.7544	Intermediate Similarity	NPC477565
0.7544	Intermediate Similarity	NPC103379
0.7543	Intermediate Similarity	NPC475326
0.754	Intermediate Similarity	NPC474904
0.7529	Intermediate Similarity	NPC295691
0.7529	Intermediate Similarity	NPC110416
0.7529	Intermediate Similarity	NPC189266
0.7529	Intermediate Similarity	NPC278799
0.7529	Intermediate Similarity	NPC54379
0.7529	Intermediate Similarity	NPC193949
0.7529	Intermediate Similarity	NPC2413
0.7529	Intermediate Similarity	NPC127674
0.7529	Intermediate Similarity	NPC469817
0.7529	Intermediate Similarity	NPC184026
0.7529	Intermediate Similarity	NPC172765
0.7529	Intermediate Similarity	NPC249797
0.7529	Intermediate Similarity	NPC276588
0.7529	Intermediate Similarity	NPC204828
0.7529	Intermediate Similarity	NPC39701
0.7529	Intermediate Similarity	NPC207757
0.7529	Intermediate Similarity	NPC5238
0.7528	Intermediate Similarity	NPC78222
0.7528	Intermediate Similarity	NPC212794
0.7528	Intermediate Similarity	NPC196447
0.7528	Intermediate Similarity	NPC253043
0.7528	Intermediate Similarity	NPC306843
0.7528	Intermediate Similarity	NPC477563
0.7528	Intermediate Similarity	NPC136508
0.7528	Intermediate Similarity	NPC168409
0.7528	Intermediate Similarity	NPC13504
0.7528	Intermediate Similarity	NPC96603
0.7515	Intermediate Similarity	NPC185838

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 NPC283999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	599
0.2-0.3	856
0.3-0.4	2154
0.4-0.5	2856
0.5-0.6	1905
0.6-0.7	590
0.7-0.8	25
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
0.75	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6071	Discontinued
0.7456	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4584	Approved
0.7427	Intermediate Similarity	NPD7020	Approved
0.7427	Intermediate Similarity	NPD7019	Approved
0.7381	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4772	Phase 2
0.7371	Intermediate Similarity	NPD4773	Phase 2
0.7353	Intermediate Similarity	NPD3692	Discontinued
0.7348	Intermediate Similarity	NPD2970	Approved
0.7348	Intermediate Similarity	NPD2969	Approved
0.7345	Intermediate Similarity	NPD2563	Approved
0.7345	Intermediate Similarity	NPD2560	Approved
0.7322	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2489	Approved
0.7308	Intermediate Similarity	NPD27	Approved
0.7308	Intermediate Similarity	NPD2898	Approved
0.7257	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6107	Approved
0.7211	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3051	Approved
0.7186	Intermediate Similarity	NPD4097	Suspended
0.7184	Intermediate Similarity	NPD6090	Discontinued
0.7167	Intermediate Similarity	NPD5604	Discontinued
0.7143	Intermediate Similarity	NPD4727	Phase 1
0.7135	Intermediate Similarity	NPD7298	Approved
0.712	Intermediate Similarity	NPD4481	Phase 3
0.7101	Intermediate Similarity	NPD4108	Discontinued
0.7092	Intermediate Similarity	NPD4420	Approved
0.709	Intermediate Similarity	NPD7311	Approved
0.709	Intermediate Similarity	NPD7281	Phase 3
0.709	Intermediate Similarity	NPD7310	Approved
0.709	Intermediate Similarity	NPD7312	Approved
0.709	Intermediate Similarity	NPD7280	Phase 3
0.709	Intermediate Similarity	NPD7313	Approved
0.7059	Intermediate Similarity	NPD7827	Phase 1
0.7053	Intermediate Similarity	NPD8054	Approved
0.7053	Intermediate Similarity	NPD7309	Approved
0.7053	Intermediate Similarity	NPD8053	Approved
0.7047	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6030	Approved
0.7045	Intermediate Similarity	NPD3033	Phase 2
0.7045	Intermediate Similarity	NPD6031	Approved
0.7035	Intermediate Similarity	NPD5005	Approved
0.7035	Intermediate Similarity	NPD5006	Approved
0.7031	Intermediate Similarity	NPD7906	Approved
0.7011	Intermediate Similarity	NPD4166	Phase 2
0.7011	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8156	Discontinued
0.7	Intermediate Similarity	NPD5772	Approved
0.7	Intermediate Similarity	NPD5773	Approved
0.7	Intermediate Similarity	NPD2978	Approved
0.7	Intermediate Similarity	NPD2977	Approved
0.699	Remote Similarity	NPD5582	Discontinued
0.6983	Remote Similarity	NPD6072	Discontinued
0.6978	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7833	Phase 2
0.6978	Remote Similarity	NPD7831	Phase 2
0.6971	Remote Similarity	NPD2421	Approved
0.6971	Remote Similarity	NPD2420	Approved
0.6963	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5241	Discontinued
0.6952	Remote Similarity	NPD8251	Approved
0.6952	Remote Similarity	NPD8099	Discontinued
0.6952	Remote Similarity	NPD8252	Approved
0.6949	Remote Similarity	NPD3640	Phase 3
0.6949	Remote Similarity	NPD3639	Approved
0.6949	Remote Similarity	NPD3641	Approved
0.6944	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5709	Phase 3
0.694	Remote Similarity	NPD7400	Phase 3
0.6938	Remote Similarity	NPD3763	Approved
0.6936	Remote Similarity	NPD5177	Phase 3
0.6932	Remote Similarity	NPD1424	Approved
0.6932	Remote Similarity	NPD2874	Phase 2
0.6923	Remote Similarity	NPD7296	Approved
0.6919	Remote Similarity	NPD3656	Approved
0.6919	Remote Similarity	NPD4010	Discontinued
0.6911	Remote Similarity	NPD4578	Approved
0.6911	Remote Similarity	NPD4577	Approved
0.6906	Remote Similarity	NPD6064	Phase 1
0.6906	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6037	Discontinued
0.6902	Remote Similarity	NPD4666	Phase 3
0.6898	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5754	Discontinued
0.6891	Remote Similarity	NPD4663	Approved
0.6882	Remote Similarity	NPD2157	Approved
0.6879	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7479	Phase 2
0.6875	Remote Similarity	NPD3124	Discontinued
0.6872	Remote Similarity	NPD4017	Approved
0.6872	Remote Similarity	NPD4005	Discontinued
0.6865	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2238	Phase 2
0.6863	Remote Similarity	NPD4859	Phase 1
0.6851	Remote Similarity	NPD4227	Discontinued
0.6842	Remote Similarity	NPD6297	Approved
0.6837	Remote Similarity	NPD3601	Discontinued
0.6836	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6788	Approved
0.6831	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6747	Phase 1
0.6825	Remote Similarity	NPD5313	Approved
0.6825	Remote Similarity	NPD5312	Approved
0.6821	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5267	Discontinued
0.6811	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD839	Approved
0.6805	Remote Similarity	NPD840	Approved
0.6805	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD3119	Phase 1
0.6804	Remote Similarity	NPD4951	Discontinued
0.6804	Remote Similarity	NPD3120	Approved
0.6802	Remote Similarity	NPD1753	Discontinued
0.68	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6851	Approved
0.6788	Remote Similarity	NPD6853	Approved
0.6786	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7598	Phase 2
0.678	Remote Similarity	NPD6087	Phase 1
0.6769	Remote Similarity	NPD3349	Phase 2
0.6768	Remote Similarity	NPD4771	Phase 2
0.6765	Remote Similarity	NPD3110	Approved
0.6765	Remote Similarity	NPD3109	Approved
0.6763	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5160	Discontinued
0.6755	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1039	Discontinued
0.6742	Remote Similarity	NPD4123	Phase 3
0.674	Remote Similarity	NPD4675	Approved
0.674	Remote Similarity	NPD4678	Approved
0.6737	Remote Similarity	NPD42	Phase 2
0.6737	Remote Similarity	NPD6042	Phase 2
0.6723	Remote Similarity	NPD3845	Phase 1
0.6717	Remote Similarity	NPD7262	Phase 1
0.6716	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2674	Phase 3
0.6706	Remote Similarity	NPD4474	Approved
0.6706	Remote Similarity	NPD4475	Approved
0.6705	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6331	Phase 2
0.6705	Remote Similarity	NPD6380	Phase 1
0.6705	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD2676	Approved
0.6704	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD52	Approved
0.6704	Remote Similarity	NPD2675	Approved
0.6704	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7526	Approved
0.6703	Remote Similarity	NPD4064	Discontinued
0.6703	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5190	Phase 2
0.6702	Remote Similarity	NPD4083	Discontinued
0.6701	Remote Similarity	NPD2488	Approved
0.6701	Remote Similarity	NPD2490	Approved
0.67	Remote Similarity	NPD4605	Approved
0.67	Remote Similarity	NPD4604	Approved
0.67	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7153	Discontinued
0.6686	Remote Similarity	NPD4257	Approved
0.6686	Remote Similarity	NPD4256	Phase 2
0.6686	Remote Similarity	NPD7037	Approved
0.6684	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3983	Phase 3
0.6684	Remote Similarity	NPD7291	Discontinued
0.6667	Remote Similarity	NPD2230	Approved
0.6667	Remote Similarity	NPD2677	Approved
0.6667	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7007	Discovery
0.6667	Remote Similarity	NPD2233	Approved
0.6667	Remote Similarity	NPD7248	Discontinued
0.6667	Remote Similarity	NPD2161	Phase 2
0.6667	Remote Similarity	NPD3156	Discontinued
0.6667	Remote Similarity	NPD4796	Discontinued
0.6667	Remote Similarity	NPD2232	Approved
0.6651	Remote Similarity	NPD3816	Phase 1
0.6651	Remote Similarity	NPD3815	Phase 1
0.6649	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1742	Approved
0.6649	Remote Similarity	NPD19	Approved
0.6649	Remote Similarity	NPD4603	Phase 2
0.6649	Remote Similarity	NPD1743	Approved
0.6648	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3157	Approved
0.6648	Remote Similarity	NPD2504	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