NPASS Compound

Structure

NPC205255 OpenBabel07101719152D 31 34 0 0 1 0 0 0 0 0999 V2000 4.3301 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 -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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 2.5981 -1.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 0.8660 1.5000 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 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 3.4641 -0.0000 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 1.0000 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 5.1962 -0.0000 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 0.0000 -0.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 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 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 14 1 0 0 0 0 4 27 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 9 2 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 22 2 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 23 2 0 0 0 0 15 2 1 1 0 0 0 15 27 1 0 0 0 0 16 3 1 6 0 0 0 16 24 1 0 0 0 0 16 27 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	421.23
Volume:	449.092
LogP:	5.687
LogD:	3.872
LogS:	-6.232
# Rotatable Bonds:	4
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	3.551
Fsp3:	0.385
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:	-5.094
MDCK Permeability:	2.4668068363098428e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	94.1470718383789%
Volume Distribution (VD):	0.79
Pgp-substrate:	4.5071234703063965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.59
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.451
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.217
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.596
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	5.295
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.299
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.805
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.402
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.277
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC205255

Natural Product ID:	NPC205255
*Common Name:**	Ancistrocongoline C
IUPAC Name:	(1R,3R)-5-(4,5-dimethoxy-7-methylnaphthalen-1-yl)-8-methoxy-1,2,3-trimethyl-3,4-dihydro-1H-isoquinolin-6-ol
Synonyms:	Ancistrocongoline C
Standard InCHIKey:	RNLKCMIGQLHEKX-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-21(29-5)26(18)22(11-14)30-6)25-19-12-15(2)27(4)16(3)24(19)23(31-7)13-20(25)28/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16-/m1/s1
SMILES:	COc1cc(O)c(c2c1[C@@H](C)N(C)[C@@H](C2)C)c1ccc(c2c1cc(C)cc2OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489958
PubChem CID:	636651
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
NPO33285	ancistrocladus congolensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193010]

☑ 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	>=	90.0	ug.mL-1	PMID[527758]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	19.3	ug.mL-1	PMID[527758]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	15.9	ug.mL-1	PMID[527758]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.002	ug.mL-1	PMID[527758]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>=	90.0	ug.mL-1	PMID[527758]

☑ 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 NPC205255 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	319
0.1-0.2	1553
0.2-0.3	6970
0.3-0.4	11037
0.4-0.5	4922
0.5-0.6	9662
0.6-0.7	6851
0.7-0.8	1068
0.8-0.85	222
0.85-0.9	55
0.9-0.95	21
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC119649
1.0	High Similarity	NPC230956
1.0	High Similarity	NPC271388
1.0	High Similarity	NPC235143
0.9933	High Similarity	NPC80759
0.9933	High Similarity	NPC221864
0.9933	High Similarity	NPC79402
0.961	High Similarity	NPC193853
0.961	High Similarity	NPC56887
0.961	High Similarity	NPC223077
0.96	High Similarity	NPC123323
0.9545	High Similarity	NPC209377
0.9286	High Similarity	NPC7393
0.9236	High Similarity	NPC195392
0.9221	High Similarity	NPC79328
0.9032	High Similarity	NPC29647
0.9006	High Similarity	NPC239775
0.8944	High Similarity	NPC118274
0.8944	High Similarity	NPC168753
0.8924	High Similarity	NPC60186
0.8909	High Similarity	NPC257269
0.8909	High Similarity	NPC230276
0.8875	High Similarity	NPC264850
0.8875	High Similarity	NPC13916
0.8848	High Similarity	NPC40496
0.8848	High Similarity	NPC119068
0.8812	High Similarity	NPC24465
0.875	High Similarity	NPC1229
0.875	High Similarity	NPC302245
0.875	High Similarity	NPC95426
0.875	High Similarity	NPC16357
0.8735	High Similarity	NPC474507
0.8704	High Similarity	NPC205421
0.8704	High Similarity	NPC145832
0.8704	High Similarity	NPC306555
0.8704	High Similarity	NPC474931
0.8704	High Similarity	NPC12053
0.8704	High Similarity	NPC158376
0.8704	High Similarity	NPC81218
0.8704	High Similarity	NPC117188
0.8698	High Similarity	NPC139783
0.8698	High Similarity	NPC65312
0.8696	High Similarity	NPC477563
0.8696	High Similarity	NPC96603
0.8696	High Similarity	NPC196447
0.8696	High Similarity	NPC136508
0.8696	High Similarity	NPC212794
0.8696	High Similarity	NPC13504
0.8696	High Similarity	NPC253043
0.8696	High Similarity	NPC306843
0.8696	High Similarity	NPC78222
0.865	High Similarity	NPC83198
0.865	High Similarity	NPC204908
0.8647	High Similarity	NPC22115
0.8647	High Similarity	NPC275680
0.8634	High Similarity	NPC324144
0.8616	High Similarity	NPC206736
0.8616	High Similarity	NPC195766
0.8614	High Similarity	NPC173416
0.8614	High Similarity	NPC148709
0.8614	High Similarity	NPC476577
0.8608	High Similarity	NPC244112
0.8605	High Similarity	NPC476565
0.8547	High Similarity	NPC223236
0.8547	High Similarity	NPC259350
0.8521	High Similarity	NPC258657
0.8521	High Similarity	NPC311973
0.8521	High Similarity	NPC15414
0.8521	High Similarity	NPC49075
0.8521	High Similarity	NPC271013
0.8521	High Similarity	NPC7715
0.8521	High Similarity	NPC328155
0.8521	High Similarity	NPC90998
0.8521	High Similarity	NPC290005
0.8521	High Similarity	NPC181796
0.8521	High Similarity	NPC279228
0.8521	High Similarity	NPC229373
0.8521	High Similarity	NPC54654
0.8521	High Similarity	NPC8836
0.8521	High Similarity	NPC182052
0.8521	High Similarity	NPC239824
0.8521	High Similarity	NPC290582
0.8521	High Similarity	NPC42663
0.8521	High Similarity	NPC223690
0.8521	High Similarity	NPC285931
0.8521	High Similarity	NPC251735
0.8521	High Similarity	NPC217748
0.8521	High Similarity	NPC185639
0.8521	High Similarity	NPC104196
0.8521	High Similarity	NPC222661
0.8509	High Similarity	NPC166014
0.8509	High Similarity	NPC27410
0.85	High Similarity	NPC476572
0.8497	Intermediate Similarity	NPC478093
0.8494	Intermediate Similarity	NPC152680
0.8494	Intermediate Similarity	NPC190783
0.8494	Intermediate Similarity	NPC232386
0.8491	Intermediate Similarity	NPC325871
0.8491	Intermediate Similarity	NPC99659
0.8488	Intermediate Similarity	NPC206900
0.8487	Intermediate Similarity	NPC470925
0.8481	Intermediate Similarity	NPC26601
0.8476	Intermediate Similarity	NPC150879
0.8476	Intermediate Similarity	NPC204947
0.8471	Intermediate Similarity	NPC167116
0.8471	Intermediate Similarity	NPC274716
0.8471	Intermediate Similarity	NPC254441
0.8462	Intermediate Similarity	NPC286119
0.8448	Intermediate Similarity	NPC473589
0.8448	Intermediate Similarity	NPC478092
0.8448	Intermediate Similarity	NPC30182
0.8448	Intermediate Similarity	NPC256124
0.8448	Intermediate Similarity	NPC478091
0.8438	Intermediate Similarity	NPC186063
0.8434	Intermediate Similarity	NPC149090
0.8434	Intermediate Similarity	NPC19520
0.8412	Intermediate Similarity	NPC30779
0.8397	Intermediate Similarity	NPC476151
0.8383	Intermediate Similarity	NPC66341
0.8383	Intermediate Similarity	NPC192135
0.8383	Intermediate Similarity	NPC477020
0.8382	Intermediate Similarity	NPC82763
0.8375	Intermediate Similarity	NPC189266
0.8375	Intermediate Similarity	NPC2413
0.8375	Intermediate Similarity	NPC204828
0.8375	Intermediate Similarity	NPC207757
0.8375	Intermediate Similarity	NPC249797
0.8375	Intermediate Similarity	NPC295691
0.8375	Intermediate Similarity	NPC184026
0.8375	Intermediate Similarity	NPC127674
0.8375	Intermediate Similarity	NPC276588
0.8375	Intermediate Similarity	NPC278799
0.8375	Intermediate Similarity	NPC193949
0.8375	Intermediate Similarity	NPC469817
0.8375	Intermediate Similarity	NPC5238
0.8375	Intermediate Similarity	NPC110416
0.8375	Intermediate Similarity	NPC39701
0.8375	Intermediate Similarity	NPC172765
0.8375	Intermediate Similarity	NPC54379
0.8373	Intermediate Similarity	NPC477562
0.8373	Intermediate Similarity	NPC69712
0.8373	Intermediate Similarity	NPC26240
0.8372	Intermediate Similarity	NPC57036
0.8372	Intermediate Similarity	NPC214116
0.8372	Intermediate Similarity	NPC116465
0.8372	Intermediate Similarity	NPC212237
0.8354	Intermediate Similarity	NPC134858
0.8354	Intermediate Similarity	NPC276665
0.8354	Intermediate Similarity	NPC169743
0.8354	Intermediate Similarity	NPC265473
0.8343	Intermediate Similarity	NPC320223
0.8343	Intermediate Similarity	NPC114364
0.8333	Intermediate Similarity	NPC229166
0.8333	Intermediate Similarity	NPC199465
0.8333	Intermediate Similarity	NPC128560
0.8324	Intermediate Similarity	NPC186546
0.8324	Intermediate Similarity	NPC476576
0.8323	Intermediate Similarity	NPC227060
0.8323	Intermediate Similarity	NPC317439
0.8323	Intermediate Similarity	NPC76682
0.8323	Intermediate Similarity	NPC10908
0.8323	Intermediate Similarity	NPC198498
0.8323	Intermediate Similarity	NPC317145
0.8323	Intermediate Similarity	NPC276890
0.8323	Intermediate Similarity	NPC63646
0.8323	Intermediate Similarity	NPC115284
0.8302	Intermediate Similarity	NPC81733
0.8302	Intermediate Similarity	NPC326316
0.8293	Intermediate Similarity	NPC233650
0.8291	Intermediate Similarity	NPC92541
0.8291	Intermediate Similarity	NPC477565
0.8291	Intermediate Similarity	NPC103379
0.8291	Intermediate Similarity	NPC219162
0.8284	Intermediate Similarity	NPC241704
0.8276	Intermediate Similarity	NPC274661
0.8276	Intermediate Similarity	NPC48490
0.8276	Intermediate Similarity	NPC82457
0.8276	Intermediate Similarity	NPC11296
0.8276	Intermediate Similarity	NPC175890
0.8274	Intermediate Similarity	NPC12424
0.8274	Intermediate Similarity	NPC251580
0.8274	Intermediate Similarity	NPC129518
0.8274	Intermediate Similarity	NPC41376
0.8269	Intermediate Similarity	NPC185838
0.8256	Intermediate Similarity	NPC302275
0.8253	Intermediate Similarity	NPC298979
0.8253	Intermediate Similarity	NPC210140
0.8249	Intermediate Similarity	NPC234318
0.8229	Intermediate Similarity	NPC60295
0.8229	Intermediate Similarity	NPC191132
0.8228	Intermediate Similarity	NPC428
0.8228	Intermediate Similarity	NPC135538
0.8228	Intermediate Similarity	NPC130941
0.8228	Intermediate Similarity	NPC24233
0.8228	Intermediate Similarity	NPC147390
0.8228	Intermediate Similarity	NPC476571
0.8228	Intermediate Similarity	NPC246587
0.82	Intermediate Similarity	NPC282508
0.8193	Intermediate Similarity	NPC81247
0.8193	Intermediate Similarity	NPC24264

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 NPC205255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	762
0.2-0.3	972
0.3-0.4	1902
0.4-0.5	2598
0.5-0.6	1726
0.6-0.7	819
0.7-0.8	158
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8848	High Similarity	NPD8453	Clinical (unspecified phase)
0.8521	High Similarity	NPD8053	Approved
0.8521	High Similarity	NPD8054	Approved
0.8323	Intermediate Similarity	NPD8099	Discontinued
0.8323	Intermediate Similarity	NPD8252	Approved
0.8323	Intermediate Similarity	NPD8251	Approved
0.8274	Intermediate Similarity	NPD8156	Discontinued
0.8221	Intermediate Similarity	NPD6788	Approved
0.8165	Intermediate Similarity	NPD4584	Approved
0.8101	Intermediate Similarity	NPD2420	Approved
0.8101	Intermediate Similarity	NPD2421	Approved
0.805	Intermediate Similarity	NPD7447	Phase 1
0.8013	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7212	Phase 2
0.7987	Intermediate Similarity	NPD7213	Phase 3
0.7879	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4475	Approved
0.7843	Intermediate Similarity	NPD4474	Approved
0.7778	Intermediate Similarity	NPD6090	Discontinued
0.7712	Intermediate Similarity	NPD4625	Phase 3
0.7702	Intermediate Similarity	NPD3845	Phase 1
0.7677	Intermediate Similarity	NPD2238	Phase 2
0.7677	Intermediate Similarity	NPD3109	Approved
0.7677	Intermediate Similarity	NPD3110	Approved
0.7662	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3051	Approved
0.7654	Intermediate Similarity	NPD7598	Phase 2
0.7654	Intermediate Similarity	NPD7906	Approved
0.7643	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4055	Discovery
0.7616	Intermediate Similarity	NPD2969	Approved
0.7616	Intermediate Similarity	NPD2970	Approved
0.76	Intermediate Similarity	NPD7479	Phase 2
0.7572	Intermediate Similarity	NPD2898	Approved
0.7572	Intermediate Similarity	NPD2489	Approved
0.7572	Intermediate Similarity	NPD27	Approved
0.7558	Intermediate Similarity	NPD6747	Phase 1
0.7548	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3124	Discontinued
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.7531	Intermediate Similarity	NPD5241	Discontinued
0.7531	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7833	Phase 2
0.7529	Intermediate Similarity	NPD7831	Phase 2
0.7528	Intermediate Similarity	NPD4578	Approved
0.7528	Intermediate Similarity	NPD4577	Approved
0.75	Intermediate Similarity	NPD4663	Approved
0.75	Intermediate Similarity	NPD1424	Approved
0.7485	Intermediate Similarity	NPD7400	Phase 3
0.7485	Intermediate Similarity	NPD6667	Approved
0.7485	Intermediate Similarity	NPD6666	Approved
0.7484	Intermediate Similarity	NPD5155	Approved
0.7484	Intermediate Similarity	NPD1753	Discontinued
0.7484	Intermediate Similarity	NPD5156	Approved
0.7473	Intermediate Similarity	NPD8095	Phase 1
0.7473	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6748	Discontinued
0.7469	Intermediate Similarity	NPD7466	Approved
0.7457	Intermediate Similarity	NPD4010	Discontinued
0.7457	Intermediate Similarity	NPD6071	Discontinued
0.7453	Intermediate Similarity	NPD7037	Approved
0.7443	Intermediate Similarity	NPD42	Phase 2
0.7443	Intermediate Similarity	NPD6042	Phase 2
0.744	Intermediate Similarity	NPD4773	Phase 2
0.744	Intermediate Similarity	NPD4772	Phase 2
0.743	Intermediate Similarity	NPD7311	Approved
0.743	Intermediate Similarity	NPD7312	Approved
0.743	Intermediate Similarity	NPD7310	Approved
0.743	Intermediate Similarity	NPD7313	Approved
0.7425	Intermediate Similarity	NPD4017	Approved
0.7425	Intermediate Similarity	NPD4005	Discontinued
0.7421	Intermediate Similarity	NPD2200	Suspended
0.7419	Intermediate Similarity	NPD3595	Approved
0.7419	Intermediate Similarity	NPD2606	Approved
0.7419	Intermediate Similarity	NPD2605	Approved
0.7419	Intermediate Similarity	NPD3594	Approved
0.7412	Intermediate Similarity	NPD2560	Approved
0.7412	Intermediate Similarity	NPD2563	Approved
0.7396	Intermediate Similarity	NPD7298	Approved
0.7389	Intermediate Similarity	NPD7309	Approved
0.7386	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5709	Phase 3
0.7378	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7124	Phase 2
0.7368	Intermediate Similarity	NPD2230	Approved
0.7368	Intermediate Similarity	NPD2232	Approved
0.7368	Intermediate Similarity	NPD2233	Approved
0.736	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3635	Approved
0.7355	Intermediate Similarity	NPD3636	Approved
0.7355	Intermediate Similarity	NPD3637	Approved
0.7353	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6746	Phase 2
0.7341	Intermediate Similarity	NPD4666	Phase 3
0.7333	Intermediate Similarity	NPD4093	Discontinued
0.732	Intermediate Similarity	NPD1669	Approved
0.7312	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1914	Approved
0.7305	Intermediate Similarity	NPD7427	Discontinued
0.7288	Intermediate Similarity	NPD7177	Discontinued
0.7288	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2668	Approved
0.7285	Intermediate Similarity	NPD2667	Approved
0.7284	Intermediate Similarity	NPD4725	Approved
0.7284	Intermediate Similarity	NPD4726	Approved
0.7284	Intermediate Similarity	NPD4721	Approved
0.7278	Intermediate Similarity	NPD7549	Discontinued
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4481	Phase 3
0.7273	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5303	Approved
0.7267	Intermediate Similarity	NPD5304	Approved
0.7267	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2568	Approved
0.7247	Intermediate Similarity	NPD6020	Phase 2
0.7235	Intermediate Similarity	NPD6072	Discontinued
0.7235	Intermediate Similarity	NPD7438	Suspended
0.7226	Intermediate Similarity	NPD4103	Phase 2
0.7226	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3692	Discontinued
0.7202	Intermediate Similarity	NPD3639	Approved
0.7202	Intermediate Similarity	NPD3641	Approved
0.7202	Intermediate Similarity	NPD6030	Approved
0.7202	Intermediate Similarity	NPD6031	Approved
0.7202	Intermediate Similarity	NPD3640	Phase 3
0.7195	Intermediate Similarity	NPD5177	Phase 3
0.7186	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6584	Phase 3
0.7178	Intermediate Similarity	NPD7030	Discontinued
0.7176	Intermediate Similarity	NPD4678	Approved
0.7176	Intermediate Similarity	NPD4675	Approved
0.7161	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5754	Discontinued
0.7143	Intermediate Similarity	NPD4097	Suspended
0.7143	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4257	Approved
0.7134	Intermediate Similarity	NPD4256	Phase 2
0.712	Intermediate Similarity	NPD3452	Approved
0.712	Intermediate Similarity	NPD3450	Approved
0.712	Intermediate Similarity	NPD2493	Approved
0.712	Intermediate Similarity	NPD2494	Approved
0.7108	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5718	Phase 2
0.7107	Intermediate Similarity	NPD7294	Phase 1
0.7104	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7802	Discontinued
0.7101	Intermediate Similarity	NPD4727	Phase 1
0.7097	Intermediate Similarity	NPD4749	Approved
0.7097	Intermediate Similarity	NPD2488	Approved
0.7097	Intermediate Similarity	NPD2490	Approved
0.7097	Intermediate Similarity	NPD4659	Approved
0.7091	Intermediate Similarity	NPD3060	Approved
0.709	Intermediate Similarity	NPD2973	Approved
0.709	Intermediate Similarity	NPD2975	Approved
0.709	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2974	Approved
0.7083	Intermediate Similarity	NPD7019	Approved
0.7083	Intermediate Similarity	NPD5006	Approved
0.7083	Intermediate Similarity	NPD5005	Approved
0.7083	Intermediate Similarity	NPD7020	Approved
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.7063	Intermediate Similarity	NPD7477	Discontinued
0.7059	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4108	Discontinued
0.7052	Intermediate Similarity	NPD4585	Approved
0.7045	Intermediate Similarity	NPD5677	Discontinued
0.7044	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5938	Phase 3
0.7035	Intermediate Similarity	NPD5089	Approved
0.7035	Intermediate Similarity	NPD5090	Approved
0.7029	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4583	Approved
0.701	Intermediate Similarity	NPD4582	Approved
0.7006	Intermediate Similarity	NPD4098	Discontinued
0.7006	Intermediate Similarity	NPD5160	Discontinued
0.7	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4236	Phase 3
0.6988	Remote Similarity	NPD4237	Approved
0.6987	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6582	Phase 2
0.6987	Remote Similarity	NPD6583	Phase 3
0.6982	Remote Similarity	NPD3157	Approved
0.6982	Remote Similarity	NPD3158	Phase 1

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