NPASS Compound

Structure

NPC56887 OpenBabel07101718222D 30 33 0 0 1 0 0 0 0 0999 V2000 0.0000 -3.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 1.7321 0.0000 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 1.7321 -3.0000 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 -1.7321 -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 -2.5981 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 2 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 -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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 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 0.0000 -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 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 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 8 2 0 0 0 0 7 9 1 0 0 0 0 8 17 1 0 0 0 0 9 19 2 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 2 1 1 0 0 0 14 26 1 0 0 0 0 15 3 1 6 0 0 0 15 22 1 0 0 0 0 15 26 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 0 0 0 0 20 23 2 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 24 25 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.21
Volume:	431.796
LogP:	5.574
LogD:	3.895
LogS:	-6.669
# Rotatable Bonds:	4
TPSA:	59.95
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	3.611
Fsp3:	0.36
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:	-5.618
MDCK Permeability:	1.8621831259224564e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.375

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.104
Plasma Protein Binding (PPB):	87.25030517578125%
Volume Distribution (VD):	1.073
Pgp-substrate:	8.323760032653809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.398
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.646
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.23
CYP3A4-substrate:	0.895

ADMET: Excretion

Clearance (CL):	2.373
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.61
Rat Oral Acute Toxicity:	0.497
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.09
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.798

Download Data

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

Natural Product: NPC56887

Natural Product ID:	NPC56887
*Common Name:**	Ancistrocongoline D
IUPAC Name:	(1R,3R)-7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
Synonyms:	Ancistrocongoline D
Standard InCHIKey:	RPYYNECGOSGRFR-HUUCEWRRSA-N
Standard InCHI:	InChI=1S/C25H29NO4/c1-13-10-20(29-5)23-17(8-7-9-19(23)28-4)21(13)24-18(27)12-16-11-14(2)26-15(3)22(16)25(24)30-6/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15-/m1/s1
SMILES:	COc1c2[C@@H](C)N[C@@H](Cc2cc(c1c1c(C)cc(c2c1cccc2OC)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489959
PubChem CID:	10409129
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	=	27.7	ug.mL-1	PMID[531221]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	30.1	ug.mL-1	PMID[531221]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	5.86	ug.mL-1	PMID[531221]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1.983	ug.mL-1	PMID[531221]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	30.0	ug.mL-1	PMID[531221]

☑ 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 NPC56887 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	318
0.1-0.2	1558
0.2-0.3	7519
0.3-0.4	10444
0.4-0.5	5399
0.5-0.6	10659
0.6-0.7	5746
0.7-0.8	848
0.8-0.85	139
0.85-0.9	20
0.9-0.95	17
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193853
1.0	High Similarity	NPC223077
0.9935	High Similarity	NPC209377
0.9673	High Similarity	NPC7393
0.9615	High Similarity	NPC195392
0.961	High Similarity	NPC205255
0.961	High Similarity	NPC119649
0.961	High Similarity	NPC230956
0.961	High Similarity	NPC271388
0.961	High Similarity	NPC235143
0.9608	High Similarity	NPC79328
0.9548	High Similarity	NPC79402
0.9548	High Similarity	NPC80759
0.9545	High Similarity	NPC221864
0.9416	High Similarity	NPC29647
0.9268	High Similarity	NPC257269
0.9226	High Similarity	NPC123323
0.9207	High Similarity	NPC40496
0.9207	High Similarity	NPC119068
0.9152	High Similarity	NPC230276
0.9091	High Similarity	NPC474507
0.897	High Similarity	NPC148709
0.897	High Similarity	NPC476577
0.897	High Similarity	NPC173416
0.8947	High Similarity	NPC476565
0.8889	High Similarity	NPC259350
0.8889	High Similarity	NPC223236
0.8834	High Similarity	NPC204947
0.8735	High Similarity	NPC66341
0.8735	High Similarity	NPC477020
0.8735	High Similarity	NPC192135
0.8727	High Similarity	NPC69712
0.8727	High Similarity	NPC477562
0.8727	High Similarity	NPC26240
0.8713	High Similarity	NPC57036
0.8678	High Similarity	NPC256124
0.8675	High Similarity	NPC239775
0.8663	High Similarity	NPC476576
0.8663	High Similarity	NPC186546
0.8614	High Similarity	NPC118274
0.8614	High Similarity	NPC168753
0.8589	High Similarity	NPC60186
0.8545	High Similarity	NPC81247
0.8545	High Similarity	NPC35627
0.8545	High Similarity	NPC13916
0.8545	High Similarity	NPC264850
0.8545	High Similarity	NPC476573
0.8506	High Similarity	NPC175890
0.8506	High Similarity	NPC274661
0.8506	High Similarity	NPC82457
0.8506	High Similarity	NPC48490
0.8506	High Similarity	NPC11296
0.85	High Similarity	NPC114124
0.8485	Intermediate Similarity	NPC24465
0.848	Intermediate Similarity	NPC32413
0.848	Intermediate Similarity	NPC474506
0.8471	Intermediate Similarity	NPC23219
0.8457	Intermediate Similarity	NPC60295
0.8457	Intermediate Similarity	NPC191132
0.8439	Intermediate Similarity	NPC302245
0.8439	Intermediate Similarity	NPC95426
0.8439	Intermediate Similarity	NPC16357
0.8424	Intermediate Similarity	NPC1229
0.8421	Intermediate Similarity	NPC258695
0.8421	Intermediate Similarity	NPC470879
0.8412	Intermediate Similarity	NPC112575
0.8409	Intermediate Similarity	NPC117717
0.8405	Intermediate Similarity	NPC206736
0.8405	Intermediate Similarity	NPC195766
0.8391	Intermediate Similarity	NPC65312
0.8391	Intermediate Similarity	NPC139783
0.8383	Intermediate Similarity	NPC474931
0.8383	Intermediate Similarity	NPC12053
0.8383	Intermediate Similarity	NPC306555
0.8383	Intermediate Similarity	NPC145832
0.8383	Intermediate Similarity	NPC117188
0.8383	Intermediate Similarity	NPC205421
0.8383	Intermediate Similarity	NPC81218
0.8383	Intermediate Similarity	NPC158376
0.8382	Intermediate Similarity	NPC135772
0.8373	Intermediate Similarity	NPC306843
0.8373	Intermediate Similarity	NPC253043
0.8373	Intermediate Similarity	NPC96603
0.8373	Intermediate Similarity	NPC196447
0.8373	Intermediate Similarity	NPC212794
0.8373	Intermediate Similarity	NPC477563
0.8373	Intermediate Similarity	NPC78222
0.8373	Intermediate Similarity	NPC136508
0.8373	Intermediate Similarity	NPC13504
0.8372	Intermediate Similarity	NPC312918
0.8372	Intermediate Similarity	NPC477561
0.8372	Intermediate Similarity	NPC155442
0.8372	Intermediate Similarity	NPC476574
0.8353	Intermediate Similarity	NPC477558
0.8344	Intermediate Similarity	NPC126519
0.8344	Intermediate Similarity	NPC170503
0.8344	Intermediate Similarity	NPC203784
0.8343	Intermediate Similarity	NPC22115
0.8343	Intermediate Similarity	NPC275680
0.8333	Intermediate Similarity	NPC83198
0.8333	Intermediate Similarity	NPC2295
0.8333	Intermediate Similarity	NPC477564
0.8333	Intermediate Similarity	NPC204908
0.8314	Intermediate Similarity	NPC243454
0.8314	Intermediate Similarity	NPC475479
0.8313	Intermediate Similarity	NPC324144
0.8313	Intermediate Similarity	NPC207824
0.8313	Intermediate Similarity	NPC60538
0.8282	Intermediate Similarity	NPC244112
0.8266	Intermediate Similarity	NPC239584
0.8246	Intermediate Similarity	NPC329969
0.8218	Intermediate Similarity	NPC223690
0.8218	Intermediate Similarity	NPC185639
0.8218	Intermediate Similarity	NPC104196
0.8218	Intermediate Similarity	NPC54654
0.8218	Intermediate Similarity	NPC290005
0.8218	Intermediate Similarity	NPC181796
0.8218	Intermediate Similarity	NPC285931
0.8218	Intermediate Similarity	NPC311973
0.8218	Intermediate Similarity	NPC222661
0.8218	Intermediate Similarity	NPC42663
0.8218	Intermediate Similarity	NPC271013
0.8218	Intermediate Similarity	NPC258657
0.8218	Intermediate Similarity	NPC217748
0.8218	Intermediate Similarity	NPC49075
0.8218	Intermediate Similarity	NPC279228
0.8218	Intermediate Similarity	NPC7715
0.8218	Intermediate Similarity	NPC8836
0.8218	Intermediate Similarity	NPC90998
0.8218	Intermediate Similarity	NPC328155
0.8218	Intermediate Similarity	NPC182052
0.8218	Intermediate Similarity	NPC15414
0.8218	Intermediate Similarity	NPC239824
0.8218	Intermediate Similarity	NPC229373
0.8218	Intermediate Similarity	NPC290582
0.8218	Intermediate Similarity	NPC251735
0.821	Intermediate Similarity	NPC277669
0.821	Intermediate Similarity	NPC76213
0.8202	Intermediate Similarity	NPC478093
0.8193	Intermediate Similarity	NPC166014
0.8193	Intermediate Similarity	NPC27410
0.8192	Intermediate Similarity	NPC206900
0.8187	Intermediate Similarity	NPC190783
0.8187	Intermediate Similarity	NPC232386
0.8187	Intermediate Similarity	NPC152680
0.8182	Intermediate Similarity	NPC476572
0.8176	Intermediate Similarity	NPC6152
0.8176	Intermediate Similarity	NPC152212
0.8171	Intermediate Similarity	NPC254441
0.8171	Intermediate Similarity	NPC167116
0.8171	Intermediate Similarity	NPC99659
0.8171	Intermediate Similarity	NPC325871
0.8171	Intermediate Similarity	NPC274716
0.8166	Intermediate Similarity	NPC150879
0.8161	Intermediate Similarity	NPC286119
0.816	Intermediate Similarity	NPC26601
0.8156	Intermediate Similarity	NPC30182
0.8156	Intermediate Similarity	NPC473589
0.8156	Intermediate Similarity	NPC478091
0.8156	Intermediate Similarity	NPC478092
0.8153	Intermediate Similarity	NPC470925
0.8148	Intermediate Similarity	NPC265473
0.8148	Intermediate Similarity	NPC276665
0.8129	Intermediate Similarity	NPC19520
0.8129	Intermediate Similarity	NPC149090
0.8121	Intermediate Similarity	NPC186063
0.8114	Intermediate Similarity	NPC30779
0.809	Intermediate Similarity	NPC82763
0.8079	Intermediate Similarity	NPC214116
0.8079	Intermediate Similarity	NPC212237
0.8079	Intermediate Similarity	NPC116465
0.8075	Intermediate Similarity	NPC476151
0.8061	Intermediate Similarity	NPC39701
0.8061	Intermediate Similarity	NPC276588
0.8061	Intermediate Similarity	NPC110416
0.8061	Intermediate Similarity	NPC189266
0.8061	Intermediate Similarity	NPC469817
0.8061	Intermediate Similarity	NPC204828
0.8061	Intermediate Similarity	NPC193949
0.8061	Intermediate Similarity	NPC249797
0.8061	Intermediate Similarity	NPC5238
0.8061	Intermediate Similarity	NPC127674
0.8061	Intermediate Similarity	NPC172765
0.8061	Intermediate Similarity	NPC295691
0.8061	Intermediate Similarity	NPC184026
0.8061	Intermediate Similarity	NPC54379
0.8061	Intermediate Similarity	NPC207757
0.8061	Intermediate Similarity	NPC278799
0.8061	Intermediate Similarity	NPC2413
0.8047	Intermediate Similarity	NPC169743
0.8047	Intermediate Similarity	NPC134858
0.8046	Intermediate Similarity	NPC320223
0.8046	Intermediate Similarity	NPC114364
0.8045	Intermediate Similarity	NPC475754
0.8035	Intermediate Similarity	NPC128560
0.8035	Intermediate Similarity	NPC199465
0.8035	Intermediate Similarity	NPC229166
0.8023	Intermediate Similarity	NPC227060
0.8023	Intermediate Similarity	NPC10908
0.8023	Intermediate Similarity	NPC63646

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 NPC56887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	726
0.2-0.3	1010
0.3-0.4	1886
0.4-0.5	2650
0.5-0.6	1729
0.6-0.7	815
0.7-0.8	136
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
0.9207	High Similarity	NPD8453	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD8054	Approved
0.8218	Intermediate Similarity	NPD8053	Approved
0.8063	Intermediate Similarity	NPD3845	Phase 1
0.8023	Intermediate Similarity	NPD8099	Discontinued
0.8023	Intermediate Similarity	NPD8252	Approved
0.8023	Intermediate Similarity	NPD8251	Approved
0.7977	Intermediate Similarity	NPD8156	Discontinued
0.7917	Intermediate Similarity	NPD6788	Approved
0.7901	Intermediate Similarity	NPD7598	Phase 2
0.7853	Intermediate Similarity	NPD4584	Approved
0.7829	Intermediate Similarity	NPD7479	Phase 2
0.7791	Intermediate Similarity	NPD2421	Approved
0.7791	Intermediate Similarity	NPD2420	Approved
0.7744	Intermediate Similarity	NPD1424	Approved
0.7744	Intermediate Similarity	NPD7447	Phase 1
0.773	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5709	Phase 3
0.7702	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7213	Phase 3
0.7683	Intermediate Similarity	NPD7212	Phase 2
0.7674	Intermediate Similarity	NPD4666	Phase 3
0.767	Intermediate Similarity	NPD42	Phase 2
0.767	Intermediate Similarity	NPD6042	Phase 2
0.7633	Intermediate Similarity	NPD7298	Approved
0.761	Intermediate Similarity	NPD2568	Approved
0.7593	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6030	Approved
0.7545	Intermediate Similarity	NPD6031	Approved
0.7532	Intermediate Similarity	NPD4474	Approved
0.7532	Intermediate Similarity	NPD4475	Approved
0.7516	Intermediate Similarity	NPD4625	Phase 3
0.7514	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6090	Discontinued
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4055	Discovery
0.7456	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4727	Phase 1
0.7439	Intermediate Similarity	NPD3060	Approved
0.7416	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7906	Approved
0.7386	Intermediate Similarity	NPD3051	Approved
0.7384	Intermediate Similarity	NPD4585	Approved
0.7375	Intermediate Similarity	NPD3110	Approved
0.7375	Intermediate Similarity	NPD2238	Phase 2
0.7375	Intermediate Similarity	NPD3109	Approved
0.7353	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5160	Discontinued
0.7346	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2970	Approved
0.7345	Intermediate Similarity	NPD2969	Approved
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.7312	Intermediate Similarity	NPD6405	Approved
0.7312	Intermediate Similarity	NPD6407	Approved
0.7303	Intermediate Similarity	NPD2489	Approved
0.7303	Intermediate Similarity	NPD27	Approved
0.7303	Intermediate Similarity	NPD2898	Approved
0.7288	Intermediate Similarity	NPD6747	Phase 1
0.7284	Intermediate Similarity	NPD3054	Approved
0.7284	Intermediate Similarity	NPD3052	Approved
0.7283	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4257	Approved
0.7273	Intermediate Similarity	NPD4256	Phase 2
0.7268	Intermediate Similarity	NPD4577	Approved
0.7268	Intermediate Similarity	NPD4578	Approved
0.7262	Intermediate Similarity	NPD3124	Discontinued
0.7257	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7831	Phase 2
0.7257	Intermediate Similarity	NPD7833	Phase 2
0.7251	Intermediate Similarity	NPD4005	Discontinued
0.725	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2677	Approved
0.7246	Intermediate Similarity	NPD5241	Discontinued
0.7246	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4663	Approved
0.7225	Intermediate Similarity	NPD8095	Phase 1
0.7219	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3158	Phase 1
0.7219	Intermediate Similarity	NPD3157	Approved
0.7216	Intermediate Similarity	NPD7400	Phase 3
0.7212	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6666	Approved
0.7202	Intermediate Similarity	NPD6667	Approved
0.7198	Intermediate Similarity	NPD6297	Approved
0.7195	Intermediate Similarity	NPD2156	Approved
0.7195	Intermediate Similarity	NPD2155	Approved
0.7195	Intermediate Similarity	NPD1753	Discontinued
0.7195	Intermediate Similarity	NPD2154	Approved
0.7191	Intermediate Similarity	NPD6071	Discontinued
0.7191	Intermediate Similarity	NPD4010	Discontinued
0.7188	Intermediate Similarity	NPD5156	Approved
0.7188	Intermediate Similarity	NPD5155	Approved
0.7186	Intermediate Similarity	NPD7466	Approved
0.7186	Intermediate Similarity	NPD6748	Discontinued
0.7184	Intermediate Similarity	NPD2977	Approved
0.7184	Intermediate Similarity	NPD2978	Approved
0.7178	Intermediate Similarity	NPD4097	Suspended
0.7175	Intermediate Similarity	NPD6746	Phase 2
0.7174	Intermediate Similarity	NPD7313	Approved
0.7174	Intermediate Similarity	NPD7311	Approved
0.7174	Intermediate Similarity	NPD7310	Approved
0.7174	Intermediate Similarity	NPD7312	Approved
0.7169	Intermediate Similarity	NPD7037	Approved
0.7168	Intermediate Similarity	NPD6072	Discontinued
0.7168	Intermediate Similarity	NPD4772	Phase 2
0.7168	Intermediate Similarity	NPD4773	Phase 2
0.7161	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6087	Phase 1
0.7151	Intermediate Similarity	NPD4017	Approved
0.7143	Intermediate Similarity	NPD2560	Approved
0.7143	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2563	Approved
0.7135	Intermediate Similarity	NPD7309	Approved
0.7135	Intermediate Similarity	NPD5976	Discontinued
0.7134	Intermediate Similarity	NPD3554	Approved
0.7134	Intermediate Similarity	NPD3555	Approved
0.7134	Intermediate Similarity	NPD3552	Approved
0.7134	Intermediate Similarity	NPD2200	Suspended
0.7134	Intermediate Similarity	NPD1669	Approved
0.7134	Intermediate Similarity	NPD3553	Approved
0.7126	Intermediate Similarity	NPD2458	Approved
0.7126	Intermediate Similarity	NPD2460	Phase 3
0.7126	Intermediate Similarity	NPD2459	Approved
0.7125	Intermediate Similarity	NPD3594	Approved
0.7125	Intermediate Similarity	NPD3595	Approved
0.7125	Intermediate Similarity	NPD2606	Approved
0.7125	Intermediate Similarity	NPD2605	Approved
0.712	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2874	Phase 2
0.7118	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7693	Approved
0.7108	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD599	Approved
0.7107	Intermediate Similarity	NPD602	Approved
0.7104	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7124	Phase 2
0.7101	Intermediate Similarity	NPD3122	Phase 3
0.7081	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2230	Approved
0.707	Intermediate Similarity	NPD2233	Approved
0.707	Intermediate Similarity	NPD2232	Approved
0.7069	Intermediate Similarity	NPD7438	Suspended
0.7068	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3636	Approved
0.7063	Intermediate Similarity	NPD3637	Approved
0.7063	Intermediate Similarity	NPD3635	Approved
0.705	Intermediate Similarity	NPD7827	Phase 1
0.7044	Intermediate Similarity	NPD1135	Approved
0.7044	Intermediate Similarity	NPD3053	Approved
0.7044	Intermediate Similarity	NPD1133	Approved
0.7044	Intermediate Similarity	NPD1129	Approved
0.7044	Intermediate Similarity	NPD1131	Approved
0.7044	Intermediate Similarity	NPD3055	Approved
0.7044	Intermediate Similarity	NPD1134	Approved
0.7043	Intermediate Similarity	NPD6851	Approved
0.7043	Intermediate Similarity	NPD6853	Approved
0.7039	Intermediate Similarity	NPD6107	Approved
0.7037	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7427	Discontinued
0.7035	Intermediate Similarity	NPD1914	Approved
0.7033	Intermediate Similarity	NPD7177	Discontinued
0.7032	Intermediate Similarity	NPD4093	Discontinued
0.7027	Intermediate Similarity	NPD7549	Discontinued
0.7027	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3638	Discontinued
0.7024	Intermediate Similarity	NPD4162	Approved
0.7019	Intermediate Similarity	NPD596	Approved
0.7019	Intermediate Similarity	NPD600	Approved
0.7018	Intermediate Similarity	NPD7019	Approved
0.7018	Intermediate Similarity	NPD7020	Approved
0.7017	Intermediate Similarity	NPD4481	Phase 3
0.7017	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4726	Approved
0.7006	Intermediate Similarity	NPD4721	Approved
0.7006	Intermediate Similarity	NPD4725	Approved
0.7	Intermediate Similarity	NPD858	Approved
0.7	Intermediate Similarity	NPD859	Approved
0.6995	Remote Similarity	NPD6020	Phase 2
0.6995	Remote Similarity	NPD4873	Discontinued
0.6989	Remote Similarity	NPD6064	Phase 1
0.6989	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2668	Approved
0.6987	Remote Similarity	NPD2667	Approved
0.6977	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.697	Remote Similarity	NPD817	Approved
0.697	Remote Similarity	NPD2989	Phase 2
0.697	Remote Similarity	NPD2986	Phase 2
0.697	Remote Similarity	NPD823	Approved
0.6968	Remote Similarity	NPD5304	Approved
0.6968	Remote Similarity	NPD5303	Approved
0.6962	Remote Similarity	NPD2561	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