NPASS Compound

Structure

NPC209377 OpenBabel07101719252D 28 31 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 20 2 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 12 2 1 6 0 0 0 12 24 1 0 0 0 0 13 3 1 1 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 26 1 0 0 0 0 19 22 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	262.07
Volume:	266.912
LogP:	3.091
LogD:	2.696
LogS:	-4.271
# Rotatable Bonds:	1
TPSA:	65.45
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.487
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.093
MDCK Permeability:	1.4272326552600134e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.415

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.359
Plasma Protein Binding (PPB):	99.4985580444336%
Volume Distribution (VD):	0.384
Pgp-substrate:	1.161363959312439%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.52
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.633
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.367
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.448
CYP3A4-substrate:	0.596

ADMET: Excretion

Clearance (CL):	0.625
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.468
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.487
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.6
Carcinogencity:	0.501
Eye Corrosion:	0.004
Eye Irritation:	0.891
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC209377

Natural Product ID:	NPC209377
*Common Name:**	Korupensamine A
IUPAC Name:	(1R,3R)-5-(4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
Synonyms:
Standard InCHIKey:	JOXWHCNNDTWJPX-CHWSQXEVSA-N
Standard InCHI:	InChI=1S/C23H25NO4/c1-11-7-15-14(5-6-17(25)23(15)20(8-11)28-4)22-16-9-12(2)24-13(3)21(16)18(26)10-19(22)27/h5-8,10,12-13,24-27H,9H2,1-4H3/t12-,13-/m1/s1
SMILES:	COc1cc(C)cc2c1c(O)ccc2c1c(O)cc(c2c1C[C@@H](C)N[C@@H]2C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487392
PubChem CID:	392421
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO20256	Ancistrocladus likoko	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076547]
NPO40017	Ancistrocladus ealaensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087584]
NPO33285	ancistrocladus congolensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193010]
NPO40017	Ancistrocladus ealaensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29560715]
NPO40017	Ancistrocladus ealaensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31630523]
NPO20256	Ancistrocladus likoko	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	7
MIC	2

Activity Type	# Activity
Cell Line	2
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	MIC	=	100.0	ug.mL-1	PMID[515831]
NPT839	Cell Line	L6	Rattus norvegicus	MIC	=	38.0	ug.mL-1	PMID[515832]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.024	ug.mL-1	PMID[515831]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.072	ug.mL-1	PMID[515831]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	25.1	ug.mL-1	PMID[515832]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	14.5	ug.mL-1	PMID[515832]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	>	1.87	ug.mL-1	PMID[515832]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.164	ug.mL-1	PMID[515832]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	820.0	nM	PMID[515833]

☑ 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 NPC209377 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	337
0.1-0.2	1686
0.2-0.3	8276
0.3-0.4	9587
0.4-0.5	5685
0.5-0.6	11018
0.6-0.7	5180
0.7-0.8	726
0.8-0.85	145
0.85-0.9	12
0.9-0.95	25
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC223077
0.9935	High Similarity	NPC193853
0.9935	High Similarity	NPC56887
0.9677	High Similarity	NPC195392
0.9671	High Similarity	NPC79328
0.9608	High Similarity	NPC7393
0.9608	High Similarity	NPC221864
0.9545	High Similarity	NPC230956
0.9545	High Similarity	NPC235143
0.9545	High Similarity	NPC205255
0.9545	High Similarity	NPC271388
0.9545	High Similarity	NPC119649
0.9484	High Similarity	NPC79402
0.9484	High Similarity	NPC80759
0.9477	High Similarity	NPC29647
0.9264	High Similarity	NPC40496
0.9264	High Similarity	NPC119068
0.9207	High Similarity	NPC230276
0.9207	High Similarity	NPC257269
0.9161	High Similarity	NPC123323
0.903	High Similarity	NPC474507
0.8909	High Similarity	NPC173416
0.8909	High Similarity	NPC476577
0.8909	High Similarity	NPC148709
0.8889	High Similarity	NPC476565
0.883	High Similarity	NPC259350
0.883	High Similarity	NPC223236
0.8773	High Similarity	NPC204947
0.8675	High Similarity	NPC66341
0.8675	High Similarity	NPC192135
0.8675	High Similarity	NPC477020
0.8667	High Similarity	NPC69712
0.8667	High Similarity	NPC477562
0.8667	High Similarity	NPC26240
0.8655	High Similarity	NPC57036
0.8621	High Similarity	NPC256124
0.8614	High Similarity	NPC239775
0.8605	High Similarity	NPC476576
0.8605	High Similarity	NPC186546
0.8598	High Similarity	NPC35627
0.8598	High Similarity	NPC476573
0.8598	High Similarity	NPC81247
0.8554	High Similarity	NPC118274
0.8554	High Similarity	NPC168753
0.8528	High Similarity	NPC60186
0.8485	Intermediate Similarity	NPC264850
0.8485	Intermediate Similarity	NPC13916
0.8448	Intermediate Similarity	NPC82457
0.8448	Intermediate Similarity	NPC48490
0.8448	Intermediate Similarity	NPC175890
0.8448	Intermediate Similarity	NPC274661
0.8448	Intermediate Similarity	NPC11296
0.8438	Intermediate Similarity	NPC114124
0.8424	Intermediate Similarity	NPC24465
0.8421	Intermediate Similarity	NPC32413
0.8421	Intermediate Similarity	NPC474506
0.8412	Intermediate Similarity	NPC23219
0.84	Intermediate Similarity	NPC191132
0.84	Intermediate Similarity	NPC60295
0.8395	Intermediate Similarity	NPC170503
0.8395	Intermediate Similarity	NPC126519
0.8395	Intermediate Similarity	NPC203784
0.8385	Intermediate Similarity	NPC477564
0.8385	Intermediate Similarity	NPC2295
0.8382	Intermediate Similarity	NPC95426
0.8382	Intermediate Similarity	NPC302245
0.8382	Intermediate Similarity	NPC16357
0.8365	Intermediate Similarity	NPC207824
0.8365	Intermediate Similarity	NPC60538
0.8364	Intermediate Similarity	NPC324144
0.8364	Intermediate Similarity	NPC1229
0.8363	Intermediate Similarity	NPC258695
0.8363	Intermediate Similarity	NPC470879
0.8353	Intermediate Similarity	NPC112575
0.8352	Intermediate Similarity	NPC117717
0.8344	Intermediate Similarity	NPC206736
0.8344	Intermediate Similarity	NPC195766
0.8333	Intermediate Similarity	NPC65312
0.8333	Intermediate Similarity	NPC139783
0.8324	Intermediate Similarity	NPC135772
0.8323	Intermediate Similarity	NPC158376
0.8323	Intermediate Similarity	NPC12053
0.8323	Intermediate Similarity	NPC205421
0.8323	Intermediate Similarity	NPC117188
0.8323	Intermediate Similarity	NPC306555
0.8323	Intermediate Similarity	NPC145832
0.8323	Intermediate Similarity	NPC474931
0.8323	Intermediate Similarity	NPC81218
0.8314	Intermediate Similarity	NPC312918
0.8314	Intermediate Similarity	NPC477561
0.8314	Intermediate Similarity	NPC476574
0.8314	Intermediate Similarity	NPC155442
0.8313	Intermediate Similarity	NPC253043
0.8313	Intermediate Similarity	NPC196447
0.8313	Intermediate Similarity	NPC96603
0.8313	Intermediate Similarity	NPC212794
0.8313	Intermediate Similarity	NPC477563
0.8313	Intermediate Similarity	NPC306843
0.8313	Intermediate Similarity	NPC13504
0.8313	Intermediate Similarity	NPC136508
0.8313	Intermediate Similarity	NPC78222
0.8294	Intermediate Similarity	NPC477558
0.8286	Intermediate Similarity	NPC22115
0.8286	Intermediate Similarity	NPC275680
0.8274	Intermediate Similarity	NPC83198
0.8274	Intermediate Similarity	NPC204908
0.8261	Intermediate Similarity	NPC277669
0.8261	Intermediate Similarity	NPC76213
0.8256	Intermediate Similarity	NPC475479
0.8256	Intermediate Similarity	NPC243454
0.8242	Intermediate Similarity	NPC166014
0.8242	Intermediate Similarity	NPC27410
0.8225	Intermediate Similarity	NPC152212
0.8221	Intermediate Similarity	NPC244112
0.821	Intermediate Similarity	NPC26601
0.8208	Intermediate Similarity	NPC239584
0.8205	Intermediate Similarity	NPC470925
0.8187	Intermediate Similarity	NPC329969
0.8171	Intermediate Similarity	NPC186063
0.8161	Intermediate Similarity	NPC49075
0.8161	Intermediate Similarity	NPC271013
0.8161	Intermediate Similarity	NPC15414
0.8161	Intermediate Similarity	NPC42663
0.8161	Intermediate Similarity	NPC90998
0.8161	Intermediate Similarity	NPC229373
0.8161	Intermediate Similarity	NPC328155
0.8161	Intermediate Similarity	NPC104196
0.8161	Intermediate Similarity	NPC7715
0.8161	Intermediate Similarity	NPC54654
0.8161	Intermediate Similarity	NPC239824
0.8161	Intermediate Similarity	NPC8836
0.8161	Intermediate Similarity	NPC222661
0.8161	Intermediate Similarity	NPC290005
0.8161	Intermediate Similarity	NPC251735
0.8161	Intermediate Similarity	NPC185639
0.8161	Intermediate Similarity	NPC217748
0.8161	Intermediate Similarity	NPC182052
0.8161	Intermediate Similarity	NPC258657
0.8161	Intermediate Similarity	NPC311973
0.8161	Intermediate Similarity	NPC181796
0.8161	Intermediate Similarity	NPC290582
0.8161	Intermediate Similarity	NPC285931
0.8161	Intermediate Similarity	NPC279228
0.8161	Intermediate Similarity	NPC223690
0.8146	Intermediate Similarity	NPC478093
0.8136	Intermediate Similarity	NPC206900
0.8129	Intermediate Similarity	NPC232386
0.8129	Intermediate Similarity	NPC152680
0.8129	Intermediate Similarity	NPC190783
0.8125	Intermediate Similarity	NPC476151
0.8121	Intermediate Similarity	NPC476572
0.8118	Intermediate Similarity	NPC6152
0.8114	Intermediate Similarity	NPC167116
0.8114	Intermediate Similarity	NPC254441
0.8114	Intermediate Similarity	NPC274716
0.811	Intermediate Similarity	NPC193949
0.811	Intermediate Similarity	NPC39701
0.811	Intermediate Similarity	NPC99659
0.811	Intermediate Similarity	NPC204828
0.811	Intermediate Similarity	NPC2413
0.811	Intermediate Similarity	NPC127674
0.811	Intermediate Similarity	NPC276588
0.811	Intermediate Similarity	NPC249797
0.811	Intermediate Similarity	NPC469817
0.811	Intermediate Similarity	NPC184026
0.811	Intermediate Similarity	NPC189266
0.811	Intermediate Similarity	NPC5238
0.811	Intermediate Similarity	NPC295691
0.811	Intermediate Similarity	NPC110416
0.811	Intermediate Similarity	NPC207757
0.811	Intermediate Similarity	NPC325871
0.811	Intermediate Similarity	NPC54379
0.811	Intermediate Similarity	NPC278799
0.811	Intermediate Similarity	NPC172765
0.8107	Intermediate Similarity	NPC150879
0.8103	Intermediate Similarity	NPC286119
0.8101	Intermediate Similarity	NPC473589
0.8101	Intermediate Similarity	NPC478091
0.8101	Intermediate Similarity	NPC478092
0.8101	Intermediate Similarity	NPC30182
0.8095	Intermediate Similarity	NPC134858
0.8086	Intermediate Similarity	NPC265473
0.8086	Intermediate Similarity	NPC276665
0.807	Intermediate Similarity	NPC149090
0.807	Intermediate Similarity	NPC19520
0.8057	Intermediate Similarity	NPC30779
0.8047	Intermediate Similarity	NPC86144
0.8047	Intermediate Similarity	NPC304659
0.8037	Intermediate Similarity	NPC326316
0.8037	Intermediate Similarity	NPC81733
0.8036	Intermediate Similarity	NPC233650
0.8034	Intermediate Similarity	NPC82763
0.8025	Intermediate Similarity	NPC92541
0.8025	Intermediate Similarity	NPC219162
0.8025	Intermediate Similarity	NPC103379
0.8025	Intermediate Similarity	NPC477565
0.8023	Intermediate Similarity	NPC116465
0.8023	Intermediate Similarity	NPC212237
0.8023	Intermediate Similarity	NPC214116
0.8	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 NPC209377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	738
0.2-0.3	1042
0.3-0.4	1844
0.4-0.5	2681
0.5-0.6	1726
0.6-0.7	785
0.7-0.8	138
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9264	High Similarity	NPD8453	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD8053	Approved
0.8161	Intermediate Similarity	NPD8054	Approved
0.8113	Intermediate Similarity	NPD3845	Phase 1
0.7965	Intermediate Similarity	NPD8099	Discontinued
0.7965	Intermediate Similarity	NPD8252	Approved
0.7965	Intermediate Similarity	NPD8251	Approved
0.795	Intermediate Similarity	NPD7598	Phase 2
0.7919	Intermediate Similarity	NPD8156	Discontinued
0.7901	Intermediate Similarity	NPD4584	Approved
0.7874	Intermediate Similarity	NPD7479	Phase 2
0.7857	Intermediate Similarity	NPD6788	Approved
0.784	Intermediate Similarity	NPD2420	Approved
0.784	Intermediate Similarity	NPD2421	Approved
0.7778	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5709	Phase 3
0.775	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD4666	Phase 3
0.7714	Intermediate Similarity	NPD42	Phase 2
0.7714	Intermediate Similarity	NPD6042	Phase 2
0.7683	Intermediate Similarity	NPD1424	Approved
0.7683	Intermediate Similarity	NPD7447	Phase 1
0.7679	Intermediate Similarity	NPD7298	Approved
0.7658	Intermediate Similarity	NPD2568	Approved
0.764	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7212	Phase 2
0.7622	Intermediate Similarity	NPD7213	Phase 3
0.7616	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6031	Approved
0.759	Intermediate Similarity	NPD6030	Approved
0.758	Intermediate Similarity	NPD4475	Approved
0.758	Intermediate Similarity	NPD4474	Approved
0.7546	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6090	Discontinued
0.7529	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4727	Phase 1
0.7485	Intermediate Similarity	NPD3060	Approved
0.7458	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4625	Phase 3
0.7421	Intermediate Similarity	NPD3110	Approved
0.7421	Intermediate Similarity	NPD2238	Phase 2
0.7421	Intermediate Similarity	NPD3109	Approved
0.7405	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4055	Discovery
0.7396	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5160	Discontinued
0.7391	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6407	Approved
0.7358	Intermediate Similarity	NPD6405	Approved
0.7345	Intermediate Similarity	NPD27	Approved
0.7345	Intermediate Similarity	NPD2489	Approved
0.7345	Intermediate Similarity	NPD2898	Approved
0.7337	Intermediate Similarity	NPD7906	Approved
0.733	Intermediate Similarity	NPD3051	Approved
0.733	Intermediate Similarity	NPD6747	Phase 1
0.7329	Intermediate Similarity	NPD3054	Approved
0.7329	Intermediate Similarity	NPD3052	Approved
0.7326	Intermediate Similarity	NPD4585	Approved
0.7317	Intermediate Similarity	NPD4256	Phase 2
0.7317	Intermediate Similarity	NPD4257	Approved
0.7305	Intermediate Similarity	NPD3124	Discontinued
0.7299	Intermediate Similarity	NPD7831	Phase 2
0.7299	Intermediate Similarity	NPD7833	Phase 2
0.7299	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5241	Discontinued
0.7288	Intermediate Similarity	NPD2969	Approved
0.7288	Intermediate Similarity	NPD2970	Approved
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7258	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7400	Phase 3
0.7239	Intermediate Similarity	NPD2156	Approved
0.7239	Intermediate Similarity	NPD2154	Approved
0.7239	Intermediate Similarity	NPD2155	Approved
0.7239	Intermediate Similarity	NPD1753	Discontinued
0.7238	Intermediate Similarity	NPD6297	Approved
0.7233	Intermediate Similarity	NPD5155	Approved
0.7233	Intermediate Similarity	NPD5156	Approved
0.7232	Intermediate Similarity	NPD4010	Discontinued
0.7229	Intermediate Similarity	NPD6748	Discontinued
0.7225	Intermediate Similarity	NPD2977	Approved
0.7225	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2978	Approved
0.7222	Intermediate Similarity	NPD4097	Suspended
0.7213	Intermediate Similarity	NPD4577	Approved
0.7213	Intermediate Similarity	NPD4578	Approved
0.7212	Intermediate Similarity	NPD7037	Approved
0.7209	Intermediate Similarity	NPD4773	Phase 2
0.7209	Intermediate Similarity	NPD4772	Phase 2
0.7208	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6087	Phase 1
0.7193	Intermediate Similarity	NPD4017	Approved
0.7193	Intermediate Similarity	NPD4005	Discontinued
0.7189	Intermediate Similarity	NPD4663	Approved
0.7186	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2677	Approved
0.7179	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1669	Approved
0.7178	Intermediate Similarity	NPD3553	Approved
0.7178	Intermediate Similarity	NPD3554	Approved
0.7178	Intermediate Similarity	NPD3555	Approved
0.7178	Intermediate Similarity	NPD3552	Approved
0.7173	Intermediate Similarity	NPD8095	Phase 1
0.717	Intermediate Similarity	NPD2606	Approved
0.717	Intermediate Similarity	NPD2605	Approved
0.717	Intermediate Similarity	NPD3595	Approved
0.717	Intermediate Similarity	NPD3594	Approved
0.7169	Intermediate Similarity	NPD2460	Phase 3
0.7169	Intermediate Similarity	NPD2459	Approved
0.7169	Intermediate Similarity	NPD2458	Approved
0.716	Intermediate Similarity	NPD3158	Phase 1
0.716	Intermediate Similarity	NPD2874	Phase 2
0.716	Intermediate Similarity	NPD3157	Approved
0.7158	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD602	Approved
0.7152	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD599	Approved
0.7151	Intermediate Similarity	NPD7693	Approved
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7135	Intermediate Similarity	NPD6071	Discontinued
0.7126	Intermediate Similarity	NPD7466	Approved
0.712	Intermediate Similarity	NPD7313	Approved
0.712	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7311	Approved
0.712	Intermediate Similarity	NPD7310	Approved
0.712	Intermediate Similarity	NPD7312	Approved
0.7119	Intermediate Similarity	NPD6746	Phase 2
0.7117	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2232	Approved
0.7115	Intermediate Similarity	NPD2233	Approved
0.7115	Intermediate Similarity	NPD2230	Approved
0.711	Intermediate Similarity	NPD6072	Discontinued
0.711	Intermediate Similarity	NPD7438	Suspended
0.7107	Intermediate Similarity	NPD3637	Approved
0.7107	Intermediate Similarity	NPD3635	Approved
0.7107	Intermediate Similarity	NPD3636	Approved
0.7089	Intermediate Similarity	NPD1135	Approved
0.7089	Intermediate Similarity	NPD3053	Approved
0.7089	Intermediate Similarity	NPD1133	Approved
0.7089	Intermediate Similarity	NPD1134	Approved
0.7089	Intermediate Similarity	NPD1129	Approved
0.7089	Intermediate Similarity	NPD1131	Approved
0.7089	Intermediate Similarity	NPD3055	Approved
0.7086	Intermediate Similarity	NPD2560	Approved
0.7086	Intermediate Similarity	NPD2563	Approved
0.7081	Intermediate Similarity	NPD6851	Approved
0.7081	Intermediate Similarity	NPD7309	Approved
0.7081	Intermediate Similarity	NPD6853	Approved
0.7081	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6107	Approved
0.7078	Intermediate Similarity	NPD4093	Discontinued
0.7076	Intermediate Similarity	NPD1914	Approved
0.7076	Intermediate Similarity	NPD5976	Discontinued
0.7076	Intermediate Similarity	NPD7427	Discontinued
0.7073	Intermediate Similarity	NPD2200	Suspended
0.7066	Intermediate Similarity	NPD4162	Approved
0.7066	Intermediate Similarity	NPD3638	Discontinued
0.7063	Intermediate Similarity	NPD596	Approved
0.7063	Intermediate Similarity	NPD600	Approved
0.7059	Intermediate Similarity	NPD7019	Approved
0.7059	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7020	Approved
0.7059	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4725	Approved
0.7048	Intermediate Similarity	NPD4721	Approved
0.7048	Intermediate Similarity	NPD4726	Approved
0.7044	Intermediate Similarity	NPD859	Approved
0.7044	Intermediate Similarity	NPD858	Approved
0.7041	Intermediate Similarity	NPD3122	Phase 3
0.7041	Intermediate Similarity	NPD7124	Phase 2
0.7033	Intermediate Similarity	NPD6020	Phase 2
0.7033	Intermediate Similarity	NPD4873	Discontinued
0.7032	Intermediate Similarity	NPD2668	Approved
0.7032	Intermediate Similarity	NPD2667	Approved
0.703	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6064	Phase 1
0.7027	Intermediate Similarity	NPD5895	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5303	Approved
0.7013	Intermediate Similarity	NPD5304	Approved
0.7012	Intermediate Similarity	NPD823	Approved
0.7012	Intermediate Similarity	NPD2989	Phase 2
0.7012	Intermediate Similarity	NPD817	Approved
0.7012	Intermediate Similarity	NPD2986	Phase 2
0.7006	Intermediate Similarity	NPD2561	Approved
0.7006	Intermediate Similarity	NPD2562	Approved
0.7	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7827	Phase 1
0.6982	Remote Similarity	NPD3692	Discontinued
0.6981	Remote Similarity	NPD4103	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