NPASS Compound

Structure

NPC116284 OpenBabel07101718282D 27 31 0 0 1 0 0 0 0 0999 V2000 0.3179 2.2748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 2.0456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3517 1.3767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1038 2.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4093 2.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1785 3.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5831 2.7087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 21 1 0 0 0 0 5 11 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 26 1 0 0 0 0 9 27 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 12 18 1 0 0 0 0 13 5 1 1 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.12
Volume:	356.977
LogP:	3.218
LogD:	3.185
LogS:	-4.587
# Rotatable Bonds:	3
TPSA:	77.46
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.833
Synthetic Accessibility Score:	3.295
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.848
MDCK Permeability:	2.699207470868714e-05
Pgp-inhibitor:	0.116
Pgp-substrate:	0.313
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	96.34807586669922%
Volume Distribution (VD):	0.756
Pgp-substrate:	4.436406135559082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.846
CYP2C19-substrate:	0.668
CYP2C9-inhibitor:	0.286
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.541
CYP2D6-substrate:	0.681
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	10.703
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.73
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.514
Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.068
Carcinogencity:	0.298
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC116284

Natural Product ID:	NPC116284
*Common Name:**	Cathafiline
IUPAC Name:	n.a.
Synonyms:	Cathafiline
Standard InCHIKey:	HOHBOJJFTZZXDF-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C20H19NO6/c1-24-15-8-12-11(6-14(15)22)5-13-17-10(3-4-21(13)20(23)25-2)7-16-19(18(12)17)27-9-26-16/h6-8,13,22H,3-5,9H2,1-2H3/t13-/m0/s1
SMILES:	COc1cc2-c3c4c(CCN([C@H]4Cc2cc1O)C(=O)OC)cc1c3OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479709
PubChem CID:	44575456
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO32857	cassytha filiformis ii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677264]

☑ 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
Others	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	0.0	%	PMID[545231]

☑ 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 NPC116284 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	300
0.1-0.2	1550
0.2-0.3	6664
0.3-0.4	11425
0.4-0.5	5920
0.5-0.6	11636
0.6-0.7	4247
0.7-0.8	652
0.8-0.85	169
0.85-0.9	94
0.9-0.95	35
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC82763
0.9695	High Similarity	NPC229166
0.9695	High Similarity	NPC199465
0.9695	High Similarity	NPC128560
0.9578	High Similarity	NPC114364
0.9578	High Similarity	NPC320223
0.9349	High Similarity	NPC155442
0.9349	High Similarity	NPC312918
0.9349	High Similarity	NPC477561
0.9349	High Similarity	NPC476574
0.9273	High Similarity	NPC298979
0.9268	High Similarity	NPC16805
0.9268	High Similarity	NPC78222
0.9268	High Similarity	NPC136508
0.9268	High Similarity	NPC302527
0.9268	High Similarity	NPC212794
0.9268	High Similarity	NPC96603
0.9268	High Similarity	NPC13504
0.9268	High Similarity	NPC167546
0.9268	High Similarity	NPC306843
0.9268	High Similarity	NPC477563
0.9268	High Similarity	NPC196447
0.9268	High Similarity	NPC253043
0.924	High Similarity	NPC135772
0.9212	High Similarity	NPC476432
0.9212	High Similarity	NPC24264
0.9207	High Similarity	NPC324144
0.9157	High Similarity	NPC306555
0.9157	High Similarity	NPC474931
0.9157	High Similarity	NPC81218
0.9157	High Similarity	NPC145832
0.9157	High Similarity	NPC247389
0.9157	High Similarity	NPC158376
0.9157	High Similarity	NPC210918
0.9157	High Similarity	NPC117188
0.9157	High Similarity	NPC205421
0.9157	High Similarity	NPC12053
0.9152	High Similarity	NPC225774
0.9102	High Similarity	NPC241055
0.9096	High Similarity	NPC219341
0.908	High Similarity	NPC186546
0.908	High Similarity	NPC476576
0.907	High Similarity	NPC248642
0.9064	High Similarity	NPC126284
0.9036	High Similarity	NPC168409
0.9017	High Similarity	NPC156576
0.9	High Similarity	NPC477558
0.8994	High Similarity	NPC149090
0.8994	High Similarity	NPC19520
0.8994	High Similarity	NPC239775
0.8976	High Similarity	NPC1229
0.8971	High Similarity	NPC237579
0.897	High Similarity	NPC27410
0.897	High Similarity	NPC477559
0.897	High Similarity	NPC160298
0.897	High Similarity	NPC306902
0.897	High Similarity	NPC232924
0.897	High Similarity	NPC166014
0.897	High Similarity	NPC266753
0.8935	High Similarity	NPC6152
0.8935	High Similarity	NPC69712
0.8935	High Similarity	NPC477562
0.8935	High Similarity	NPC26240
0.8914	High Similarity	NPC57036
0.8841	High Similarity	NPC99659
0.8841	High Similarity	NPC325871
0.883	High Similarity	NPC477020
0.883	High Similarity	NPC192135
0.883	High Similarity	NPC66341
0.8824	High Similarity	NPC168753
0.8824	High Similarity	NPC118274
0.8824	High Similarity	NPC152212
0.881	High Similarity	NPC238530
0.881	High Similarity	NPC232514
0.881	High Similarity	NPC276944
0.8807	High Similarity	NPC214116
0.8795	High Similarity	NPC111485
0.8786	High Similarity	NPC118633
0.8786	High Similarity	NPC148693
0.8786	High Similarity	NPC294790
0.8735	High Similarity	NPC476572
0.869	High Similarity	NPC60186
0.8647	High Similarity	NPC81247
0.8647	High Similarity	NPC86144
0.8647	High Similarity	NPC476573
0.8647	High Similarity	NPC35627
0.8647	High Similarity	NPC304659
0.8636	High Similarity	NPC476575
0.8629	High Similarity	NPC470879
0.8629	High Similarity	NPC258695
0.8629	High Similarity	NPC220961
0.8629	High Similarity	NPC474507
0.858	High Similarity	NPC32413
0.858	High Similarity	NPC474506
0.8571	High Similarity	NPC23219
0.8563	High Similarity	NPC186063
0.8545	High Similarity	NPC81733
0.8545	High Similarity	NPC326316
0.8529	High Similarity	NPC189470
0.8523	High Similarity	NPC267408
0.8523	High Similarity	NPC32154
0.8514	High Similarity	NPC476577
0.8514	High Similarity	NPC173416
0.8514	High Similarity	NPC112575
0.8514	High Similarity	NPC148709
0.8508	High Similarity	NPC117717
0.8506	High Similarity	NPC2314
0.8453	Intermediate Similarity	NPC475754
0.8444	Intermediate Similarity	NPC474904
0.8432	Intermediate Similarity	NPC475654
0.8427	Intermediate Similarity	NPC275132
0.8409	Intermediate Similarity	NPC241704
0.8409	Intermediate Similarity	NPC237044
0.8393	Intermediate Similarity	NPC276588
0.8393	Intermediate Similarity	NPC244112
0.8393	Intermediate Similarity	NPC189266
0.8393	Intermediate Similarity	NPC127674
0.8393	Intermediate Similarity	NPC184026
0.8393	Intermediate Similarity	NPC193949
0.8393	Intermediate Similarity	NPC249797
0.8393	Intermediate Similarity	NPC207757
0.8393	Intermediate Similarity	NPC295691
0.8393	Intermediate Similarity	NPC39701
0.8393	Intermediate Similarity	NPC469817
0.8393	Intermediate Similarity	NPC172765
0.8393	Intermediate Similarity	NPC41178
0.8393	Intermediate Similarity	NPC216459
0.8393	Intermediate Similarity	NPC54379
0.8393	Intermediate Similarity	NPC5238
0.8393	Intermediate Similarity	NPC2413
0.8393	Intermediate Similarity	NPC138487
0.8393	Intermediate Similarity	NPC204828
0.8393	Intermediate Similarity	NPC278799
0.8393	Intermediate Similarity	NPC110416
0.8382	Intermediate Similarity	NPC210140
0.8382	Intermediate Similarity	NPC150879
0.8382	Intermediate Similarity	NPC190332
0.8382	Intermediate Similarity	NPC181653
0.8373	Intermediate Similarity	NPC220858
0.8373	Intermediate Similarity	NPC88249
0.8373	Intermediate Similarity	NPC192768
0.8373	Intermediate Similarity	NPC151895
0.8373	Intermediate Similarity	NPC97221
0.8372	Intermediate Similarity	NPC24465
0.8364	Intermediate Similarity	NPC24233
0.8364	Intermediate Similarity	NPC135538
0.8364	Intermediate Similarity	NPC147390
0.8364	Intermediate Similarity	NPC475959
0.8364	Intermediate Similarity	NPC246587
0.8364	Intermediate Similarity	NPC476571
0.8364	Intermediate Similarity	NPC428
0.8362	Intermediate Similarity	NPC474325
0.8352	Intermediate Similarity	NPC187678
0.8352	Intermediate Similarity	NPC304675
0.8343	Intermediate Similarity	NPC146288
0.8343	Intermediate Similarity	NPC312531
0.8324	Intermediate Similarity	NPC13916
0.8324	Intermediate Similarity	NPC124657
0.8324	Intermediate Similarity	NPC233718
0.8324	Intermediate Similarity	NPC264850
0.8315	Intermediate Similarity	NPC474745
0.8313	Intermediate Similarity	NPC477565
0.8313	Intermediate Similarity	NPC103379
0.8306	Intermediate Similarity	NPC478093
0.8306	Intermediate Similarity	NPC24260
0.8304	Intermediate Similarity	NPC205167
0.8304	Intermediate Similarity	NPC249274
0.8303	Intermediate Similarity	NPC179825
0.8303	Intermediate Similarity	NPC321505
0.8303	Intermediate Similarity	NPC191376
0.8287	Intermediate Similarity	NPC320088
0.8286	Intermediate Similarity	NPC311991
0.8276	Intermediate Similarity	NPC100566
0.8276	Intermediate Similarity	NPC204947
0.8274	Intermediate Similarity	NPC233029
0.8274	Intermediate Similarity	NPC210148
0.8274	Intermediate Similarity	NPC26601
0.8266	Intermediate Similarity	NPC134858
0.8261	Intermediate Similarity	NPC30182
0.8261	Intermediate Similarity	NPC473589
0.8261	Intermediate Similarity	NPC478091
0.8261	Intermediate Similarity	NPC478092
0.8246	Intermediate Similarity	NPC477080
0.8235	Intermediate Similarity	NPC126519
0.8235	Intermediate Similarity	NPC31311
0.8235	Intermediate Similarity	NPC170503
0.8235	Intermediate Similarity	NPC203784
0.8235	Intermediate Similarity	NPC234392
0.8208	Intermediate Similarity	NPC320104
0.8208	Intermediate Similarity	NPC233650
0.8204	Intermediate Similarity	NPC211296
0.8193	Intermediate Similarity	NPC476151
0.8182	Intermediate Similarity	NPC185838
0.8177	Intermediate Similarity	NPC46990
0.8177	Intermediate Similarity	NPC475981
0.8177	Intermediate Similarity	NPC474746
0.8176	Intermediate Similarity	NPC76079
0.8172	Intermediate Similarity	NPC24228
0.8171	Intermediate Similarity	NPC474324
0.8171	Intermediate Similarity	NPC57812

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 NPC116284 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	717
0.2-0.3	1141
0.3-0.4	2103
0.4-0.5	2700
0.5-0.6	1683
0.6-0.7	494
0.7-0.8	117
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD2421	Approved
0.8242	Intermediate Similarity	NPD2420	Approved
0.8229	Intermediate Similarity	NPD27	Approved
0.8229	Intermediate Similarity	NPD2489	Approved
0.8218	Intermediate Similarity	NPD3051	Approved
0.8171	Intermediate Similarity	NPD2970	Approved
0.8171	Intermediate Similarity	NPD2969	Approved
0.8087	Intermediate Similarity	NPD7906	Approved
0.8023	Intermediate Similarity	NPD4481	Phase 3
0.7976	Intermediate Similarity	NPD4584	Approved
0.7967	Intermediate Similarity	NPD4577	Approved
0.7967	Intermediate Similarity	NPD7310	Approved
0.7967	Intermediate Similarity	NPD7313	Approved
0.7967	Intermediate Similarity	NPD7311	Approved
0.7967	Intermediate Similarity	NPD7312	Approved
0.7967	Intermediate Similarity	NPD4578	Approved
0.7939	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4663	Approved
0.7923	Intermediate Similarity	NPD7309	Approved
0.7923	Intermediate Similarity	NPD8054	Approved
0.7923	Intermediate Similarity	NPD8053	Approved
0.7921	Intermediate Similarity	NPD2898	Approved
0.7807	Intermediate Similarity	NPD2488	Approved
0.7807	Intermediate Similarity	NPD2490	Approved
0.7737	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD4010	Discontinued
0.7692	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD3452	Approved
0.7629	Intermediate Similarity	NPD2494	Approved
0.7629	Intermediate Similarity	NPD2493	Approved
0.7629	Intermediate Similarity	NPD3450	Approved
0.7614	Intermediate Similarity	NPD2978	Approved
0.7614	Intermediate Similarity	NPD2977	Approved
0.7614	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5241	Discontinued
0.7584	Intermediate Similarity	NPD7833	Phase 2
0.7584	Intermediate Similarity	NPD7831	Phase 2
0.7584	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7280	Phase 3
0.7581	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7281	Phase 3
0.7574	Intermediate Similarity	NPD7047	Phase 3
0.7544	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3845	Phase 1
0.7541	Intermediate Similarity	NPD8099	Discontinued
0.7541	Intermediate Similarity	NPD8252	Approved
0.7541	Intermediate Similarity	NPD8251	Approved
0.7524	Intermediate Similarity	NPD6997	Phase 2
0.7514	Intermediate Similarity	NPD6071	Discontinued
0.7514	Intermediate Similarity	NPD6297	Approved
0.7513	Intermediate Similarity	NPD4582	Approved
0.7513	Intermediate Similarity	NPD4583	Approved
0.7512	Intermediate Similarity	NPD7827	Phase 1
0.75	Intermediate Similarity	NPD8156	Discontinued
0.7487	Intermediate Similarity	NPD2971	Approved
0.7487	Intermediate Similarity	NPD2968	Approved
0.7474	Intermediate Similarity	NPD4420	Approved
0.7472	Intermediate Similarity	NPD2560	Approved
0.7472	Intermediate Similarity	NPD2563	Approved
0.7462	Intermediate Similarity	NPD4002	Approved
0.7462	Intermediate Similarity	NPD4004	Approved
0.7461	Intermediate Similarity	NPD5582	Discontinued
0.7458	Intermediate Similarity	NPD7298	Approved
0.7442	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6788	Approved
0.7427	Intermediate Similarity	NPD5754	Discontinued
0.7423	Intermediate Similarity	NPD2974	Approved
0.7423	Intermediate Similarity	NPD2973	Approved
0.7423	Intermediate Similarity	NPD2975	Approved
0.7401	Intermediate Similarity	NPD4772	Phase 2
0.7401	Intermediate Similarity	NPD4773	Phase 2
0.7386	Intermediate Similarity	NPD4017	Approved
0.7371	Intermediate Similarity	NPD3640	Phase 3
0.7371	Intermediate Similarity	NPD3641	Approved
0.7371	Intermediate Similarity	NPD4727	Phase 1
0.7371	Intermediate Similarity	NPD3639	Approved
0.7356	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6851	Approved
0.7354	Intermediate Similarity	NPD6853	Approved
0.7348	Intermediate Similarity	NPD7400	Phase 3
0.734	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5006	Approved
0.7323	Intermediate Similarity	NPD5005	Approved
0.7322	Intermediate Similarity	NPD4166	Phase 2
0.731	Intermediate Similarity	NPD4580	Approved
0.7293	Intermediate Similarity	NPD5604	Discontinued
0.7259	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4040	Phase 1
0.7238	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD42	Phase 2
0.7219	Intermediate Similarity	NPD6042	Phase 2
0.7219	Intermediate Similarity	NPD5312	Approved
0.7219	Intermediate Similarity	NPD5313	Approved
0.7211	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3109	Approved
0.7202	Intermediate Similarity	NPD3110	Approved
0.7175	Intermediate Similarity	NPD6030	Approved
0.7175	Intermediate Similarity	NPD6031	Approved
0.7174	Intermediate Similarity	NPD6107	Approved
0.7156	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3057	Approved
0.715	Intermediate Similarity	NPD2491	Approved
0.715	Intermediate Similarity	NPD3448	Approved
0.7135	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6723	Discontinued
0.7126	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4666	Phase 3
0.7118	Intermediate Similarity	NPD2492	Phase 1
0.7104	Intermediate Similarity	NPD4055	Discovery
0.7093	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3533	Approved
0.7065	Intermediate Similarity	NPD5709	Phase 3
0.7065	Intermediate Similarity	NPD2972	Approved
0.7062	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4107	Approved
0.7048	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6666	Approved
0.7045	Intermediate Similarity	NPD6667	Approved
0.7039	Intermediate Similarity	NPD4210	Discontinued
0.7024	Intermediate Similarity	NPD5156	Approved
0.7024	Intermediate Similarity	NPD5155	Approved
0.7022	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6090	Discontinued
0.7021	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7802	Discontinued
0.6984	Remote Similarity	NPD7177	Discontinued
0.6982	Remote Similarity	NPD5718	Phase 2
0.6976	Remote Similarity	NPD4859	Phase 1
0.6974	Remote Similarity	NPD3349	Phase 2
0.6973	Remote Similarity	NPD6234	Discontinued
0.6971	Remote Similarity	NPD3060	Approved
0.6971	Remote Similarity	NPD5177	Phase 3
0.6971	Remote Similarity	NPD4237	Approved
0.6971	Remote Similarity	NPD4236	Phase 3
0.6965	Remote Similarity	NPD6612	Phase 2
0.6964	Remote Similarity	NPD2605	Approved
0.6964	Remote Similarity	NPD3594	Approved
0.6964	Remote Similarity	NPD3595	Approved
0.6964	Remote Similarity	NPD2606	Approved
0.6963	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7048	Phase 3
0.6954	Remote Similarity	NPD4721	Approved
0.6954	Remote Similarity	NPD4725	Approved
0.6954	Remote Similarity	NPD7296	Approved
0.6954	Remote Similarity	NPD4726	Approved
0.6952	Remote Similarity	NPD6747	Phase 1
0.6947	Remote Similarity	NPD8153	Approved
0.6947	Remote Similarity	NPD8152	Approved
0.6941	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2674	Phase 3
0.6936	Remote Similarity	NPD1753	Discontinued
0.6931	Remote Similarity	NPD4482	Phase 3
0.6923	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7110	Phase 1
0.6919	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3885	Approved
0.6906	Remote Similarity	NPD4005	Discontinued
0.6906	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD824	Approved
0.6905	Remote Similarity	NPD3635	Approved
0.6905	Remote Similarity	NPD3636	Approved
0.6905	Remote Similarity	NPD3637	Approved
0.6904	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7907	Approved
0.6895	Remote Similarity	NPD7228	Approved
0.6893	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7549	Discontinued
0.6889	Remote Similarity	NPD5976	Discontinued
0.6889	Remote Similarity	NPD1914	Approved
0.6888	Remote Similarity	NPD7291	Discontinued
0.6887	Remote Similarity	NPD3763	Approved
0.6885	Remote Similarity	NPD37	Approved
0.6881	Remote Similarity	NPD5457	Discontinued
0.6875	Remote Similarity	NPD5676	Approved
0.6875	Remote Similarity	NPD6674	Discontinued
0.6872	Remote Similarity	NPD1424	Approved
0.6859	Remote Similarity	NPD4873	Discontinued
0.6857	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5772	Approved
0.6848	Remote Similarity	NPD5773	Approved
0.6845	Remote Similarity	NPD5677	Discontinued
0.6842	Remote Similarity	NPD4474	Approved
0.6842	Remote Similarity	NPD4475	Approved
0.6839	Remote Similarity	NPD4108	Discontinued
0.6832	Remote Similarity	NPD8095	Phase 1
0.6825	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7037	Approved
0.6816	Remote Similarity	NPD3124	Discontinued
0.6811	Remote Similarity	NPD5977	Approved
0.6811	Remote Similarity	NPD5978	Approved
0.6808	Remote Similarity	NPD4665	Approved
0.6808	Remote Similarity	NPD4111	Phase 1
0.6804	Remote Similarity	NPD7132	Clinical (unspecified phase)

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