NPASS Compound

Structure

NPC123323 OpenBabel07101718182D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.7321 1.0000 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 3.4641 -0.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -3.5000 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 0.8660 -1.5000 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 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 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 -1.7321 -3.0000 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 1.7321 1.0000 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 -0.8660 -0.5000 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 -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 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 15 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 2 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 22 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 2 1 1 0 0 0 16 28 1 0 0 0 0 17 3 1 6 0 0 0 17 25 1 0 0 0 0 17 28 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 20 29 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 0 0 0 0 23 27 2 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	435.24
Volume:	466.388
LogP:	5.653
LogD:	3.657
LogS:	-6.452
# Rotatable Bonds:	5
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	3.509
Fsp3:	0.407
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.088
MDCK Permeability:	4.856886880588718e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.709

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	64.499755859375%
Volume Distribution (VD):	0.827
Pgp-substrate:	12.147257804870605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.205
CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.262
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.457
CYP2D6-substrate:	0.947
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.935

ADMET: Excretion

Clearance (CL):	8.303
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.833
AMES Toxicity:	0.367
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.092
Carcinogencity:	0.11
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC123323

Natural Product ID:	NPC123323
*Common Name:**	O,N-Dimethylancistrocladine
IUPAC Name:	(1S,3S)-5-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-6,8-dimethoxy-1,2,3-trimethyl-3,4-dihydro-1H-isoquinoline
Synonyms:	O,N-Dimethylancistrocladine
Standard InCHIKey:	KKJVVBRCACGMIS-IRXDYDNUSA-N
Standard InCHI:	InChI=1S/C27H33NO4/c1-15-12-21(30-6)26-18(10-9-11-20(26)29-5)24(15)27-19-13-16(2)28(4)17(3)25(19)22(31-7)14-23(27)32-8/h9-12,14,16-17H,13H2,1-8H3/t16-,17-/m0/s1
SMILES:	Cc1cc(c2c(cccc2OC)c1c1c2C[C@H](C)N(C)[C@@H](C)c2c(cc1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464728
PubChem CID:	11224334
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
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510589]
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14510589]
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165131]

☑ 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	4
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	MIC	=	42.9	ug.mL-1	PMID[494778]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.6	ug.mL-1	PMID[494778]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	34.1	ug.mL-1	PMID[494778]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	65.3	ug.mL-1	PMID[494778]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	5.4	ug.mL-1	PMID[494778]

☑ 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 NPC123323 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	384
0.1-0.2	1718
0.2-0.3	8343
0.3-0.4	9560
0.4-0.5	5688
0.5-0.6	11224
0.6-0.7	4833
0.7-0.8	698
0.8-0.85	166
0.85-0.9	62
0.9-0.95	10
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC119649
0.96	High Similarity	NPC235143
0.96	High Similarity	NPC271388
0.96	High Similarity	NPC205255
0.96	High Similarity	NPC230956
0.9536	High Similarity	NPC80759
0.9536	High Similarity	NPC79402
0.9533	High Similarity	NPC221864
0.9533	High Similarity	NPC7393
0.9226	High Similarity	NPC193853
0.9226	High Similarity	NPC56887
0.9226	High Similarity	NPC223077
0.9161	High Similarity	NPC209377
0.8861	High Similarity	NPC195392
0.8839	High Similarity	NPC79328
0.8831	High Similarity	NPC244112
0.8718	High Similarity	NPC476572
0.8716	High Similarity	NPC470925
0.871	High Similarity	NPC99659
0.871	High Similarity	NPC325871
0.8688	High Similarity	NPC204947
0.8667	High Similarity	NPC230276
0.8667	High Similarity	NPC257269
0.8654	High Similarity	NPC29647
0.8642	High Similarity	NPC149090
0.8642	High Similarity	NPC239775
0.8642	High Similarity	NPC10908
0.8642	High Similarity	NPC63646
0.8642	High Similarity	NPC115284
0.8642	High Similarity	NPC198498
0.8642	High Similarity	NPC317439
0.8642	High Similarity	NPC227060
0.8642	High Similarity	NPC76682
0.8642	High Similarity	NPC276890
0.8642	High Similarity	NPC19520
0.8642	High Similarity	NPC317145
0.8606	High Similarity	NPC119068
0.8606	High Similarity	NPC40496
0.8589	High Similarity	NPC12424
0.8589	High Similarity	NPC251580
0.8589	High Similarity	NPC129518
0.8589	High Similarity	NPC41376
0.858	High Similarity	NPC168753
0.858	High Similarity	NPC118274
0.8571	High Similarity	NPC276665
0.8571	High Similarity	NPC265473
0.8563	High Similarity	NPC302275
0.8553	High Similarity	NPC60186
0.8516	High Similarity	NPC81733
0.8516	High Similarity	NPC326316
0.8512	High Similarity	NPC95426
0.8512	High Similarity	NPC302245
0.8512	High Similarity	NPC16357
0.8509	High Similarity	NPC13916
0.8509	High Similarity	NPC264850
0.8506	High Similarity	NPC219162
0.8506	High Similarity	NPC92541
0.8485	Intermediate Similarity	NPC293093
0.8462	Intermediate Similarity	NPC65312
0.8462	Intermediate Similarity	NPC139783
0.8447	Intermediate Similarity	NPC24465
0.8442	Intermediate Similarity	NPC130941
0.8412	Intermediate Similarity	NPC275680
0.8412	Intermediate Similarity	NPC22115
0.8395	Intermediate Similarity	NPC476432
0.8395	Intermediate Similarity	NPC24264
0.8385	Intermediate Similarity	NPC1229
0.8383	Intermediate Similarity	NPC243454
0.8383	Intermediate Similarity	NPC475479
0.8383	Intermediate Similarity	NPC474507
0.8377	Intermediate Similarity	NPC51957
0.8377	Intermediate Similarity	NPC253883
0.8377	Intermediate Similarity	NPC106295
0.8377	Intermediate Similarity	NPC16107
0.8377	Intermediate Similarity	NPC95075
0.8377	Intermediate Similarity	NPC210437
0.8377	Intermediate Similarity	NPC90844
0.8377	Intermediate Similarity	NPC476144
0.8377	Intermediate Similarity	NPC144863
0.8372	Intermediate Similarity	NPC476565
0.8353	Intermediate Similarity	NPC47077
0.8353	Intermediate Similarity	NPC14507
0.8344	Intermediate Similarity	NPC81218
0.8344	Intermediate Similarity	NPC117188
0.8344	Intermediate Similarity	NPC205421
0.8344	Intermediate Similarity	NPC247389
0.8344	Intermediate Similarity	NPC158376
0.8344	Intermediate Similarity	NPC306555
0.8344	Intermediate Similarity	NPC145832
0.8344	Intermediate Similarity	NPC114124
0.8344	Intermediate Similarity	NPC474931
0.8344	Intermediate Similarity	NPC12053
0.8333	Intermediate Similarity	NPC306843
0.8333	Intermediate Similarity	NPC253043
0.8333	Intermediate Similarity	NPC302527
0.8333	Intermediate Similarity	NPC196447
0.8333	Intermediate Similarity	NPC16805
0.8333	Intermediate Similarity	NPC96603
0.8333	Intermediate Similarity	NPC477563
0.8333	Intermediate Similarity	NPC212794
0.8333	Intermediate Similarity	NPC167546
0.8333	Intermediate Similarity	NPC13504
0.8333	Intermediate Similarity	NPC32413
0.8333	Intermediate Similarity	NPC225774
0.8333	Intermediate Similarity	NPC239584
0.8333	Intermediate Similarity	NPC78222
0.8333	Intermediate Similarity	NPC136508
0.8333	Intermediate Similarity	NPC474506
0.8323	Intermediate Similarity	NPC7467
0.8323	Intermediate Similarity	NPC23219
0.8314	Intermediate Similarity	NPC259350
0.8314	Intermediate Similarity	NPC223236
0.8293	Intermediate Similarity	NPC83198
0.8293	Intermediate Similarity	NPC204908
0.8284	Intermediate Similarity	NPC49075
0.8284	Intermediate Similarity	NPC285931
0.8284	Intermediate Similarity	NPC279228
0.8284	Intermediate Similarity	NPC90998
0.8284	Intermediate Similarity	NPC258657
0.8284	Intermediate Similarity	NPC217748
0.8284	Intermediate Similarity	NPC182052
0.8284	Intermediate Similarity	NPC311973
0.8284	Intermediate Similarity	NPC299990
0.8284	Intermediate Similarity	NPC229373
0.8284	Intermediate Similarity	NPC290582
0.8284	Intermediate Similarity	NPC7715
0.8284	Intermediate Similarity	NPC104196
0.8284	Intermediate Similarity	NPC222661
0.8284	Intermediate Similarity	NPC8836
0.8284	Intermediate Similarity	NPC290005
0.8284	Intermediate Similarity	NPC328155
0.8284	Intermediate Similarity	NPC15414
0.8284	Intermediate Similarity	NPC239824
0.8284	Intermediate Similarity	NPC251735
0.8284	Intermediate Similarity	NPC185639
0.8284	Intermediate Similarity	NPC54654
0.8284	Intermediate Similarity	NPC223690
0.8284	Intermediate Similarity	NPC181796
0.8284	Intermediate Similarity	NPC42663
0.8284	Intermediate Similarity	NPC73492
0.8284	Intermediate Similarity	NPC271013
0.8282	Intermediate Similarity	NPC219341
0.8274	Intermediate Similarity	NPC470879
0.8274	Intermediate Similarity	NPC258695
0.8272	Intermediate Similarity	NPC324144
0.8266	Intermediate Similarity	NPC478093
0.8263	Intermediate Similarity	NPC112575
0.8263	Intermediate Similarity	NPC148709
0.8263	Intermediate Similarity	NPC173416
0.8263	Intermediate Similarity	NPC476577
0.8256	Intermediate Similarity	NPC206900
0.825	Intermediate Similarity	NPC195766
0.825	Intermediate Similarity	NPC206736
0.8235	Intermediate Similarity	NPC254441
0.8235	Intermediate Similarity	NPC274716
0.8235	Intermediate Similarity	NPC167116
0.8232	Intermediate Similarity	NPC150879
0.8232	Intermediate Similarity	NPC210918
0.8225	Intermediate Similarity	NPC195538
0.8225	Intermediate Similarity	NPC286119
0.8224	Intermediate Similarity	NPC213206
0.8224	Intermediate Similarity	NPC188163
0.8224	Intermediate Similarity	NPC474915
0.8224	Intermediate Similarity	NPC328750
0.8218	Intermediate Similarity	NPC478091
0.8218	Intermediate Similarity	NPC478092
0.8218	Intermediate Similarity	NPC256124
0.8218	Intermediate Similarity	NPC30182
0.8218	Intermediate Similarity	NPC473589
0.8187	Intermediate Similarity	NPC126519
0.8187	Intermediate Similarity	NPC249996
0.8187	Intermediate Similarity	NPC203784
0.8187	Intermediate Similarity	NPC170503
0.8176	Intermediate Similarity	NPC30779
0.8176	Intermediate Similarity	NPC476202
0.8158	Intermediate Similarity	NPC314682
0.8148	Intermediate Similarity	NPC477559
0.8148	Intermediate Similarity	NPC27410
0.8148	Intermediate Similarity	NPC166014
0.8148	Intermediate Similarity	NPC160298
0.8148	Intermediate Similarity	NPC266753
0.8148	Intermediate Similarity	NPC306902
0.8148	Intermediate Similarity	NPC232924
0.8144	Intermediate Similarity	NPC152680
0.8144	Intermediate Similarity	NPC232386
0.8144	Intermediate Similarity	NPC190783
0.814	Intermediate Similarity	NPC116465
0.814	Intermediate Similarity	NPC212237
0.814	Intermediate Similarity	NPC214116
0.8117	Intermediate Similarity	NPC128019
0.8117	Intermediate Similarity	NPC136860
0.8117	Intermediate Similarity	NPC476567
0.8113	Intermediate Similarity	NPC26601
0.811	Intermediate Similarity	NPC169743
0.8075	Intermediate Similarity	NPC186063
0.8049	Intermediate Similarity	NPC233650
0.8046	Intermediate Similarity	NPC175890
0.8046	Intermediate Similarity	NPC274661
0.8046	Intermediate Similarity	NPC11296
0.8046	Intermediate Similarity	NPC48490

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 NPC123323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	833
0.2-0.3	958
0.3-0.4	1906
0.4-0.5	2610
0.5-0.6	1778
0.6-0.7	706
0.7-0.8	124
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD8252	Approved
0.8642	High Similarity	NPD8251	Approved
0.8642	High Similarity	NPD8099	Discontinued
0.8606	High Similarity	NPD8453	Clinical (unspecified phase)
0.8589	High Similarity	NPD8156	Discontinued
0.8428	Intermediate Similarity	NPD6788	Approved
0.8377	Intermediate Similarity	NPD4584	Approved
0.8284	Intermediate Similarity	NPD8054	Approved
0.8284	Intermediate Similarity	NPD8053	Approved
0.8224	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD4474	Approved
0.8054	Intermediate Similarity	NPD4475	Approved
0.7962	Intermediate Similarity	NPD7598	Phase 2
0.7937	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3109	Approved
0.7881	Intermediate Similarity	NPD3110	Approved
0.7866	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7447	Phase 1
0.7771	Intermediate Similarity	NPD7466	Approved
0.7748	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2421	Approved
0.7736	Intermediate Similarity	NPD2420	Approved
0.7736	Intermediate Similarity	NPD3124	Discontinued
0.7735	Intermediate Similarity	NPD8095	Phase 1
0.7725	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1424	Approved
0.7683	Intermediate Similarity	NPD7298	Approved
0.7673	Intermediate Similarity	NPD7124	Phase 2
0.7665	Intermediate Similarity	NPD7400	Phase 3
0.7658	Intermediate Similarity	NPD6748	Discontinued
0.7643	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7212	Phase 2
0.7625	Intermediate Similarity	NPD7213	Phase 3
0.7613	Intermediate Similarity	NPD2200	Suspended
0.7607	Intermediate Similarity	NPD4017	Approved
0.7605	Intermediate Similarity	NPD4055	Discovery
0.7531	Intermediate Similarity	NPD6090	Discontinued
0.7529	Intermediate Similarity	NPD3051	Approved
0.7529	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4481	Phase 3
0.7438	Intermediate Similarity	NPD5754	Discontinued
0.743	Intermediate Similarity	NPD7906	Approved
0.7427	Intermediate Similarity	NPD6747	Phase 1
0.7419	Intermediate Similarity	NPD2238	Phase 2
0.741	Intermediate Similarity	NPD4773	Phase 2
0.741	Intermediate Similarity	NPD4772	Phase 2
0.7403	Intermediate Similarity	NPD5718	Phase 2
0.7403	Intermediate Similarity	NPD7294	Phase 1
0.7389	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2969	Approved
0.7384	Intermediate Similarity	NPD2970	Approved
0.7378	Intermediate Similarity	NPD3640	Phase 3
0.7378	Intermediate Similarity	NPD6030	Approved
0.7378	Intermediate Similarity	NPD3641	Approved
0.7378	Intermediate Similarity	NPD3639	Approved
0.7378	Intermediate Similarity	NPD6031	Approved
0.7371	Intermediate Similarity	NPD7479	Phase 2
0.7368	Intermediate Similarity	NPD7802	Discontinued
0.7346	Intermediate Similarity	NPD6667	Approved
0.7346	Intermediate Similarity	NPD6666	Approved
0.7346	Intermediate Similarity	NPD3845	Phase 1
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6071	Discontinued
0.7325	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7831	Phase 2
0.7294	Intermediate Similarity	NPD7833	Phase 2
0.7294	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4005	Discontinued
0.7289	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1669	Approved
0.7284	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5241	Discontinued
0.7273	Intermediate Similarity	NPD4727	Phase 1
0.7273	Intermediate Similarity	NPD1914	Approved
0.7257	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7905	Discontinued
0.7253	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2489	Approved
0.7241	Intermediate Similarity	NPD27	Approved
0.7241	Intermediate Similarity	NPD2898	Approved
0.7234	Intermediate Similarity	NPD5005	Approved
0.7234	Intermediate Similarity	NPD5006	Approved
0.7226	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4585	Approved
0.7216	Intermediate Similarity	NPD42	Phase 2
0.7216	Intermediate Similarity	NPD6042	Phase 2
0.7209	Intermediate Similarity	NPD5677	Discontinued
0.7209	Intermediate Similarity	NPD6037	Discontinued
0.7207	Intermediate Similarity	NPD7310	Approved
0.7207	Intermediate Similarity	NPD4577	Approved
0.7207	Intermediate Similarity	NPD4578	Approved
0.7207	Intermediate Similarity	NPD7312	Approved
0.7207	Intermediate Similarity	NPD7313	Approved
0.7207	Intermediate Similarity	NPD7311	Approved
0.7202	Intermediate Similarity	NPD7438	Suspended
0.719	Intermediate Similarity	NPD4098	Discontinued
0.7189	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4663	Approved
0.7176	Intermediate Similarity	NPD2560	Approved
0.7176	Intermediate Similarity	NPD2563	Approved
0.717	Intermediate Similarity	NPD6895	Approved
0.717	Intermediate Similarity	NPD6896	Approved
0.717	Intermediate Similarity	NPD6111	Discontinued
0.7169	Intermediate Similarity	NPD7427	Discontinued
0.7168	Intermediate Similarity	NPD6107	Approved
0.7167	Intermediate Similarity	NPD7309	Approved
0.7161	Intermediate Similarity	NPD4908	Phase 1
0.7161	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2668	Approved
0.7133	Intermediate Similarity	NPD2667	Approved
0.7126	Intermediate Similarity	NPD4010	Discontinued
0.7125	Intermediate Similarity	NPD1753	Discontinued
0.7118	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5155	Approved
0.7115	Intermediate Similarity	NPD5156	Approved
0.7111	Intermediate Similarity	NPD2968	Approved
0.7111	Intermediate Similarity	NPD2971	Approved
0.711	Intermediate Similarity	NPD6746	Phase 2
0.7105	Intermediate Similarity	NPD2232	Approved
0.7105	Intermediate Similarity	NPD2233	Approved
0.7105	Intermediate Similarity	NPD2230	Approved
0.7101	Intermediate Similarity	NPD6072	Discontinued
0.7099	Intermediate Similarity	NPD7037	Approved
0.7086	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3301	Approved
0.7062	Intermediate Similarity	NPD7177	Discontinued
0.7056	Intermediate Similarity	NPD7549	Discontinued
0.7052	Intermediate Similarity	NPD5709	Phase 3
0.7051	Intermediate Similarity	NPD2606	Approved
0.7051	Intermediate Similarity	NPD2605	Approved
0.7051	Intermediate Similarity	NPD3594	Approved
0.7051	Intermediate Similarity	NPD3595	Approved
0.7045	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7477	Discontinued
0.7021	Intermediate Similarity	NPD4420	Approved
0.7019	Intermediate Similarity	NPD4108	Discontinued
0.7011	Intermediate Similarity	NPD4666	Phase 3
0.7006	Intermediate Similarity	NPD5938	Phase 3
0.7006	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD5089	Approved
0.6994	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3637	Approved
0.6987	Remote Similarity	NPD3635	Approved
0.6987	Remote Similarity	NPD3636	Approved
0.6982	Remote Similarity	NPD6357	Discontinued
0.697	Remote Similarity	NPD3692	Discontinued
0.697	Remote Similarity	NPD5160	Discontinued
0.6968	Remote Similarity	NPD2973	Approved
0.6968	Remote Similarity	NPD2975	Approved
0.6968	Remote Similarity	NPD2974	Approved
0.6966	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5976	Discontinued
0.6961	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7291	Discontinued
0.6954	Remote Similarity	NPD3445	Approved
0.6954	Remote Similarity	NPD4093	Discontinued
0.6954	Remote Similarity	NPD3443	Approved
0.6954	Remote Similarity	NPD3444	Approved
0.6951	Remote Similarity	NPD44	Approved
0.6951	Remote Similarity	NPD5177	Phase 3
0.6951	Remote Similarity	NPD6364	Approved
0.6946	Remote Similarity	NPD7019	Approved
0.6946	Remote Similarity	NPD7020	Approved
0.6941	Remote Similarity	NPD4678	Approved
0.6941	Remote Similarity	NPD4675	Approved
0.6933	Remote Similarity	NPD4725	Approved
0.6933	Remote Similarity	NPD4721	Approved
0.6933	Remote Similarity	NPD4726	Approved
0.6933	Remote Similarity	NPD7030	Discontinued
0.6928	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5312	Approved
0.6927	Remote Similarity	NPD5313	Approved
0.6927	Remote Similarity	NPD6020	Phase 2
0.6923	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7110	Phase 1
0.6898	Remote Similarity	NPD7262	Phase 1
0.6897	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4097	Suspended
0.6894	Remote Similarity	NPD2568	Approved
0.6893	Remote Similarity	NPD6687	Approved
0.6893	Remote Similarity	NPD6688	Approved
0.6893	Remote Similarity	NPD5242	Approved
0.689	Remote Similarity	NPD4256	Phase 2
0.689	Remote Similarity	NPD4257	Approved
0.6887	Remote Similarity	NPD5304	Approved
0.6887	Remote Similarity	NPD5303	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