NPASS Compound

Structure

CID24260 OpenBabel06191715352D 44 51 0 0 1 0 0 0 0 0999 V2000 -2.7905 2.1071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6498 -3.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3642 1.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 -1.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5132 -2.1887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4341 0.9840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5770 -0.9952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0054 -1.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8686 0.6878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0759 1.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5261 2.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0823 -3.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3387 -2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4213 1.1427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3124 0.3666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3338 1.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8143 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6998 0.9521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1507 0.9894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9368 -2.3517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9316 0.8290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8532 1.5624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3601 -1.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2415 1.2078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 1.2736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7838 -2.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9079 0.1633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5225 -0.1943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0745 1.0224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2705 0.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8143 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0823 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0823 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8647 1.7290 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7838 -3.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8388 -0.2020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9233 1.0893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5575 0.0758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1562 0.8848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5390 -0.7931 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 37 1 0 0 0 0 2 38 1 0 0 0 0 3 40 1 0 0 0 0 4 7 1 0 0 0 0 4 21 2 0 0 0 0 5 8 2 0 0 0 0 5 21 1 0 0 0 0 6 9 2 0 0 0 0 6 22 1 0 0 0 0 7 25 2 0 0 0 0 8 25 1 0 0 0 0 9 29 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 37 1 0 0 0 0 13 38 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 22 2 0 0 0 0 16 30 1 0 0 0 0 17 23 2 0 0 0 0 17 31 1 0 0 0 0 18 24 2 0 0 0 0 18 33 1 0 0 0 0 19 26 2 0 0 0 0 19 32 1 0 0 0 0 20 41 1 0 0 0 0 20 42 1 0 0 0 0 23 26 1 0 0 0 0 24 34 1 0 0 0 0 25 43 1 0 0 0 0 26 27 1 0 0 0 0 27 15 1 1 0 0 0 27 37 1 0 0 0 0 28 14 1 1 0 0 0 28 34 1 0 0 0 0 28 38 1 0 0 0 0 29 30 2 0 0 0 0 29 39 1 0 0 0 0 30 43 1 0 0 0 0 31 32 2 0 0 0 0 31 40 1 0 0 0 0 32 44 1 0 0 0 0 33 35 2 0 0 0 0 33 41 1 0 0 0 0 34 36 2 0 0 0 0 35 36 1 0 0 0 0 35 42 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.26
Volume:	605.858
LogP:	6.164
LogD:	3.758
LogS:	-6.48
# Rotatable Bonds:	1
TPSA:	72.86
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	5.829
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.787
MDCK Permeability:	2.8693573767668568e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.292
Plasma Protein Binding (PPB):	91.70825958251953%
Volume Distribution (VD):	0.973
Pgp-substrate:	5.992823600769043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.336
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.61
CYP2D6-inhibitor:	0.196
CYP2D6-substrate:	0.954
CYP3A4-inhibitor:	0.282
CYP3A4-substrate:	0.945

ADMET: Excretion

Clearance (CL):	15.864
Half-life (T1/2):	0.191

ADMET: Toxicity

hERG Blockers:	0.953
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.438
AMES Toxicity:	0.336
Rat Oral Acute Toxicity:	0.336
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.847
Carcinogencity:	0.534
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.385

Download Data

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

Natural Product: NPC24260

Natural Product ID:	NPC24260
*Common Name:**	Cepharanoline
IUPAC Name:	n.a.
Synonyms:	Cepharanoline
Standard InCHIKey:	VQAWRQZAAIQXHM-IZLXSDGUSA-N
Standard InCHI:	InChI=1S/C36H36N2O6/c1-37-12-10-23-17-31(40-3)32-19-26(23)27(37)15-22-6-9-29(39)30(16-22)43-25-7-4-21(5-8-25)14-28-34-24(11-13-38(28)2)18-33-35(36(34)44-32)42-20-41-33/h4-9,16-19,27-28,39H,10-15,20H2,1-3H3/t27-,28+/m1/s1
SMILES:	CN1CCc2cc(c3cc2[C@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@H]1c2c(CCN1C)cc1c(c2O3)OCO1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496044
PubChem CID:	5315779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129063]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	56.0	%	PMID[480245]

☑ 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 NPC24260 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	371
0.1-0.2	1749
0.2-0.3	8354
0.3-0.4	10070
0.4-0.5	5867
0.5-0.6	8658
0.6-0.7	6222
0.7-0.8	1122
0.8-0.85	158
0.85-0.9	46
0.9-0.95	47
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC475654
0.9591	High Similarity	NPC104196
0.9591	High Similarity	NPC8836
0.9591	High Similarity	NPC290582
0.9591	High Similarity	NPC217748
0.9591	High Similarity	NPC311973
0.9591	High Similarity	NPC258657
0.9591	High Similarity	NPC73492
0.9591	High Similarity	NPC251735
0.9591	High Similarity	NPC15414
0.9591	High Similarity	NPC181796
0.9591	High Similarity	NPC7715
0.9591	High Similarity	NPC222661
0.9591	High Similarity	NPC271013
0.9591	High Similarity	NPC49075
0.9591	High Similarity	NPC239824
0.9591	High Similarity	NPC182052
0.9591	High Similarity	NPC185639
0.9591	High Similarity	NPC90998
0.9591	High Similarity	NPC299990
0.9591	High Similarity	NPC285931
0.9591	High Similarity	NPC223690
0.9591	High Similarity	NPC279228
0.9591	High Similarity	NPC328155
0.9591	High Similarity	NPC42663
0.9591	High Similarity	NPC229373
0.9591	High Similarity	NPC54654
0.9591	High Similarity	NPC290005
0.9535	High Similarity	NPC167116
0.9535	High Similarity	NPC274716
0.9535	High Similarity	NPC254441
0.9532	High Similarity	NPC286119
0.9477	High Similarity	NPC30779
0.9425	High Similarity	NPC212237
0.9425	High Similarity	NPC116465
0.9371	High Similarity	NPC275680
0.9371	High Similarity	NPC22115
0.9318	High Similarity	NPC206900
0.9318	High Similarity	NPC281581
0.9318	High Similarity	NPC11296
0.9318	High Similarity	NPC175890
0.9318	High Similarity	NPC274661
0.9318	High Similarity	NPC48490
0.9318	High Similarity	NPC82457
0.9266	High Similarity	NPC191132
0.9266	High Similarity	NPC475597
0.9266	High Similarity	NPC60295
0.9266	High Similarity	NPC473716
0.9257	High Similarity	NPC302245
0.9257	High Similarity	NPC95426
0.9257	High Similarity	NPC16357
0.9205	High Similarity	NPC65312
0.9205	High Similarity	NPC139783
0.9181	High Similarity	NPC115284
0.9181	High Similarity	NPC10908
0.9181	High Similarity	NPC227060
0.9181	High Similarity	NPC317145
0.9181	High Similarity	NPC198498
0.9181	High Similarity	NPC63646
0.9181	High Similarity	NPC76682
0.9181	High Similarity	NPC317439
0.9181	High Similarity	NPC276890
0.9128	High Similarity	NPC12424
0.9128	High Similarity	NPC251580
0.9128	High Similarity	NPC41376
0.9128	High Similarity	NPC129518
0.9106	High Similarity	NPC478093
0.9056	High Similarity	NPC473589
0.9056	High Similarity	NPC478091
0.9056	High Similarity	NPC478092
0.9056	High Similarity	NPC30182
0.9023	High Similarity	NPC293093
0.895	High Similarity	NPC256124
0.895	High Similarity	NPC85381
0.8947	High Similarity	NPC264850
0.8947	High Similarity	NPC256012
0.8947	High Similarity	NPC42549
0.8947	High Similarity	NPC240841
0.8947	High Similarity	NPC250846
0.8947	High Similarity	NPC317272
0.8947	High Similarity	NPC268503
0.8947	High Similarity	NPC13916
0.8944	High Similarity	NPC318805
0.8944	High Similarity	NPC41122
0.892	High Similarity	NPC475479
0.892	High Similarity	NPC243454
0.8889	High Similarity	NPC276944
0.8889	High Similarity	NPC24465
0.8889	High Similarity	NPC238530
0.8889	High Similarity	NPC232514
0.887	High Similarity	NPC239584
0.8852	High Similarity	NPC234318
0.8844	High Similarity	NPC83198
0.8844	High Similarity	NPC204908
0.8693	High Similarity	NPC190783
0.8693	High Similarity	NPC232386
0.8693	High Similarity	NPC152680
0.8667	High Similarity	NPC302275
0.8655	High Similarity	NPC111485
0.8636	High Similarity	NPC475215
0.8636	High Similarity	NPC108434
0.8619	High Similarity	NPC249996
0.8588	High Similarity	NPC2314
0.8579	High Similarity	NPC82763
0.8571	High Similarity	NPC254581
0.8556	High Similarity	NPC195538
0.8547	High Similarity	NPC320223
0.8547	High Similarity	NPC114364
0.8539	High Similarity	NPC128560
0.8539	High Similarity	NPC229166
0.8539	High Similarity	NPC199465
0.8538	High Similarity	NPC247639
0.8538	High Similarity	NPC25084
0.8525	High Similarity	NPC476576
0.8525	High Similarity	NPC186546
0.8508	High Similarity	NPC476202
0.848	Intermediate Similarity	NPC278799
0.848	Intermediate Similarity	NPC110416
0.848	Intermediate Similarity	NPC184026
0.848	Intermediate Similarity	NPC54379
0.848	Intermediate Similarity	NPC189266
0.848	Intermediate Similarity	NPC295691
0.848	Intermediate Similarity	NPC5238
0.848	Intermediate Similarity	NPC207757
0.848	Intermediate Similarity	NPC216459
0.848	Intermediate Similarity	NPC138487
0.848	Intermediate Similarity	NPC204828
0.848	Intermediate Similarity	NPC469817
0.848	Intermediate Similarity	NPC172765
0.848	Intermediate Similarity	NPC276588
0.848	Intermediate Similarity	NPC41178
0.848	Intermediate Similarity	NPC39701
0.848	Intermediate Similarity	NPC193949
0.848	Intermediate Similarity	NPC2413
0.848	Intermediate Similarity	NPC249797
0.848	Intermediate Similarity	NPC127674
0.847	Intermediate Similarity	NPC47077
0.847	Intermediate Similarity	NPC14507
0.843	Intermediate Similarity	NPC146288
0.8427	Intermediate Similarity	NPC239775
0.8427	Intermediate Similarity	NPC149090
0.8427	Intermediate Similarity	NPC19520
0.8371	Intermediate Similarity	NPC118274
0.8371	Intermediate Similarity	NPC168753
0.837	Intermediate Similarity	NPC57036
0.837	Intermediate Similarity	NPC214116
0.8324	Intermediate Similarity	NPC31311
0.8324	Intermediate Similarity	NPC10871
0.8324	Intermediate Similarity	NPC234392
0.8306	Intermediate Similarity	NPC116284
0.8297	Intermediate Similarity	NPC244554
0.8295	Intermediate Similarity	NPC475393
0.8268	Intermediate Similarity	NPC75958
0.8261	Intermediate Similarity	NPC135772
0.8258	Intermediate Similarity	NPC298979
0.8251	Intermediate Similarity	NPC312918
0.8251	Intermediate Similarity	NPC476574
0.8251	Intermediate Similarity	NPC155442
0.8251	Intermediate Similarity	NPC477561
0.8246	Intermediate Similarity	NPC192768
0.8246	Intermediate Similarity	NPC151895
0.8246	Intermediate Similarity	NPC220858
0.8246	Intermediate Similarity	NPC88249
0.8246	Intermediate Similarity	NPC97221
0.8242	Intermediate Similarity	NPC118633
0.8242	Intermediate Similarity	NPC148693
0.8242	Intermediate Similarity	NPC294790
0.8239	Intermediate Similarity	NPC60186
0.8232	Intermediate Similarity	NPC49353
0.8232	Intermediate Similarity	NPC187678
0.8216	Intermediate Similarity	NPC9867
0.8202	Intermediate Similarity	NPC24264
0.8202	Intermediate Similarity	NPC476432
0.82	Intermediate Similarity	NPC82056
0.8197	Intermediate Similarity	NPC32154
0.8197	Intermediate Similarity	NPC474507
0.8187	Intermediate Similarity	NPC103379
0.8187	Intermediate Similarity	NPC477565
0.8182	Intermediate Similarity	NPC119649
0.8182	Intermediate Similarity	NPC230956
0.8182	Intermediate Similarity	NPC235143
0.8182	Intermediate Similarity	NPC271388
0.8182	Intermediate Similarity	NPC205255
0.8156	Intermediate Similarity	NPC12053
0.8156	Intermediate Similarity	NPC117188
0.8156	Intermediate Similarity	NPC205421
0.8156	Intermediate Similarity	NPC306555
0.8156	Intermediate Similarity	NPC145832
0.8156	Intermediate Similarity	NPC247389
0.8156	Intermediate Similarity	NPC81218
0.8156	Intermediate Similarity	NPC158376
0.8156	Intermediate Similarity	NPC474931
0.8152	Intermediate Similarity	NPC32413
0.8152	Intermediate Similarity	NPC474506
0.8152	Intermediate Similarity	NPC257269
0.8152	Intermediate Similarity	NPC230276
0.815	Intermediate Similarity	NPC210148
0.815	Intermediate Similarity	NPC233029
0.8146	Intermediate Similarity	NPC167546
0.8146	Intermediate Similarity	NPC477563

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 NPC24260 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	754
0.2-0.3	1209
0.3-0.4	2339
0.4-0.5	2419
0.5-0.6	1537
0.6-0.7	571
0.7-0.8	103
0.8-0.85	2
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9591	High Similarity	NPD8053	Approved
0.9591	High Similarity	NPD8054	Approved
0.9181	High Similarity	NPD8099	Discontinued
0.9181	High Similarity	NPD8251	Approved
0.9181	High Similarity	NPD8252	Approved
0.9128	High Similarity	NPD8156	Discontinued
0.8263	Intermediate Similarity	NPD8095	Phase 1
0.8098	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7906	Approved
0.807	Intermediate Similarity	NPD4584	Approved
0.8023	Intermediate Similarity	NPD6788	Approved
0.7901	Intermediate Similarity	NPD6071	Discontinued
0.7861	Intermediate Similarity	NPD7310	Approved
0.7861	Intermediate Similarity	NPD7312	Approved
0.7861	Intermediate Similarity	NPD7313	Approved
0.7861	Intermediate Similarity	NPD7311	Approved
0.7824	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD7309	Approved
0.7814	Intermediate Similarity	NPD2489	Approved
0.7814	Intermediate Similarity	NPD27	Approved
0.7802	Intermediate Similarity	NPD3051	Approved
0.7797	Intermediate Similarity	NPD4772	Phase 2
0.7797	Intermediate Similarity	NPD4773	Phase 2
0.7778	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7831	Phase 2
0.7778	Intermediate Similarity	NPD7833	Phase 2
0.7766	Intermediate Similarity	NPD4577	Approved
0.7766	Intermediate Similarity	NPD4578	Approved
0.776	Intermediate Similarity	NPD2969	Approved
0.776	Intermediate Similarity	NPD2970	Approved
0.7737	Intermediate Similarity	NPD4663	Approved
0.7725	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2563	Approved
0.7667	Intermediate Similarity	NPD2560	Approved
0.7654	Intermediate Similarity	NPD7298	Approved
0.7588	Intermediate Similarity	NPD5005	Approved
0.7588	Intermediate Similarity	NPD5006	Approved
0.7584	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8153	Approved
0.7568	Intermediate Similarity	NPD8152	Approved
0.7557	Intermediate Similarity	NPD7447	Phase 1
0.7557	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7549	Discontinued
0.7525	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7827	Phase 1
0.75	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4481	Phase 3
0.7433	Intermediate Similarity	NPD2898	Approved
0.7419	Intermediate Similarity	NPD4010	Discontinued
0.7418	Intermediate Similarity	NPD2977	Approved
0.7418	Intermediate Similarity	NPD2978	Approved
0.7401	Intermediate Similarity	NPD7212	Phase 2
0.7401	Intermediate Similarity	NPD7213	Phase 3
0.7387	Intermediate Similarity	NPD4420	Approved
0.7386	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3450	Approved
0.7363	Intermediate Similarity	NPD2493	Approved
0.7363	Intermediate Similarity	NPD2494	Approved
0.7363	Intermediate Similarity	NPD3452	Approved
0.736	Intermediate Similarity	NPD1424	Approved
0.7347	Intermediate Similarity	NPD2488	Approved
0.7347	Intermediate Similarity	NPD2490	Approved
0.7341	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5677	Discontinued
0.7303	Intermediate Similarity	NPD2421	Approved
0.7303	Intermediate Similarity	NPD2420	Approved
0.7297	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4055	Discovery
0.7288	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6031	Approved
0.7278	Intermediate Similarity	NPD6030	Approved
0.7277	Intermediate Similarity	NPD6997	Phase 2
0.7273	Intermediate Similarity	NPD6107	Approved
0.7268	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4583	Approved
0.7255	Intermediate Similarity	NPD4582	Approved
0.7253	Intermediate Similarity	NPD4678	Approved
0.7253	Intermediate Similarity	NPD4675	Approved
0.7247	Intermediate Similarity	NPD7124	Phase 2
0.7238	Intermediate Similarity	NPD7047	Phase 3
0.7228	Intermediate Similarity	NPD5773	Approved
0.7228	Intermediate Similarity	NPD5772	Approved
0.7216	Intermediate Similarity	NPD7280	Phase 3
0.7216	Intermediate Similarity	NPD7281	Phase 3
0.7215	Intermediate Similarity	NPD6723	Discontinued
0.7206	Intermediate Similarity	NPD4002	Approved
0.7206	Intermediate Similarity	NPD4004	Approved
0.7204	Intermediate Similarity	NPD5604	Discontinued
0.7198	Intermediate Similarity	NPD4017	Approved
0.7191	Intermediate Similarity	NPD5241	Discontinued
0.7182	Intermediate Similarity	NPD3639	Approved
0.7182	Intermediate Similarity	NPD3641	Approved
0.7182	Intermediate Similarity	NPD3640	Phase 3
0.7181	Intermediate Similarity	NPD7802	Discontinued
0.7174	Intermediate Similarity	NPD3382	Approved
0.7174	Intermediate Similarity	NPD3384	Approved
0.7174	Intermediate Similarity	NPD3383	Approved
0.7164	Intermediate Similarity	NPD2973	Approved
0.7164	Intermediate Similarity	NPD2975	Approved
0.7164	Intermediate Similarity	NPD2974	Approved
0.7151	Intermediate Similarity	NPD3845	Phase 1
0.7151	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7466	Approved
0.7104	Intermediate Similarity	NPD4005	Discontinued
0.7083	Intermediate Similarity	NPD7228	Approved
0.7071	Intermediate Similarity	NPD6841	Approved
0.7071	Intermediate Similarity	NPD6843	Phase 3
0.7071	Intermediate Similarity	NPD6842	Approved
0.7062	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4580	Approved
0.7056	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4475	Approved
0.7052	Intermediate Similarity	NPD4474	Approved
0.7047	Intermediate Similarity	NPD5312	Approved
0.7047	Intermediate Similarity	NPD5313	Approved
0.7041	Intermediate Similarity	NPD2968	Approved
0.7041	Intermediate Similarity	NPD2971	Approved
0.7039	Intermediate Similarity	NPD6748	Discontinued
0.703	Intermediate Similarity	NPD5582	Discontinued
0.7027	Intermediate Similarity	NPD6072	Discontinued
0.7017	Intermediate Similarity	NPD7598	Phase 2
0.7011	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4040	Phase 1
0.7005	Intermediate Similarity	NPD6853	Approved
0.7005	Intermediate Similarity	NPD6851	Approved
0.7	Intermediate Similarity	NPD7199	Phase 2
0.6995	Remote Similarity	NPD2122	Discontinued
0.6994	Remote Similarity	NPD5718	Phase 2
0.6989	Remote Similarity	NPD2200	Suspended
0.6985	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4236	Phase 3
0.6983	Remote Similarity	NPD5177	Phase 3
0.6983	Remote Similarity	NPD4237	Approved
0.6978	Remote Similarity	NPD4123	Phase 3
0.6977	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6297	Approved
0.6974	Remote Similarity	NPD7007	Discovery
0.6963	Remote Similarity	NPD4166	Phase 2
0.6961	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4873	Discontinued
0.6952	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6090	Discontinued
0.6927	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7037	Approved
0.6927	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3124	Discontinued
0.6919	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1613	Approved
0.6912	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6625	Approved
0.6905	Remote Similarity	NPD7701	Phase 2
0.6904	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6234	Discontinued
0.6881	Remote Similarity	NPD7296	Approved
0.6879	Remote Similarity	NPD4908	Phase 1
0.6872	Remote Similarity	NPD42	Phase 2
0.6872	Remote Similarity	NPD6042	Phase 2
0.6869	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6667	Approved
0.6868	Remote Similarity	NPD6666	Approved
0.6856	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7074	Phase 3
0.6835	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7907	Approved
0.6832	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3692	Discontinued
0.6811	Remote Similarity	NPD5976	Discontinued
0.681	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6896	Approved
0.6798	Remote Similarity	NPD6895	Approved
0.6798	Remote Similarity	NPD6111	Discontinued
0.6796	Remote Similarity	NPD4162	Approved
0.6796	Remote Similarity	NPD6674	Discontinued
0.6796	Remote Similarity	NPD3060	Approved
0.6793	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7223	Discontinued
0.6787	Remote Similarity	NPD7224	Discontinued
0.6786	Remote Similarity	NPD7054	Approved
0.6778	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD1375	Discontinued
0.6777	Remote Similarity	NPD7584	Approved
0.6776	Remote Similarity	NPD3816	Phase 1
0.6776	Remote Similarity	NPD3815	Phase 1
0.6774	Remote Similarity	NPD4210	Discontinued
0.6772	Remote Similarity	NPD4585	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