NPASS Compound

Structure

NPC90952 OpenBabel07101719522D 37 41 0 0 1 0 0 0 0 0999 V2000 0.8257 2.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4264 -1.2136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6515 -0.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1287 -0.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8257 -2.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6515 2.8605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0484 -1.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9780 -1.5247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6515 0.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6515 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8257 -1.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4772 -0.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6515 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4772 -3.3372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0484 -3.4550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8257 1.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8401 -2.0727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6515 -2.8605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3030 -1.9070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3917 -2.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6515 -1.9070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8257 1.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8257 -0.4767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4772 -1.4302 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8257 -1.4302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3030 -2.8605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8257 -0.4767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7909 -2.1439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8257 -3.3372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3452 -2.3837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8257 0.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6515 1.9070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9780 -3.2428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 6 36 1 0 0 0 0 7 8 2 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 18 2 0 0 0 0 15 30 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 28 1 0 0 0 0 17 37 1 0 0 0 0 19 2 1 6 0 0 0 19 31 1 0 0 0 0 20 23 1 0 0 0 0 20 32 1 6 0 0 0 21 26 1 1 0 0 0 21 28 1 0 0 0 0 22 33 2 0 0 0 0 22 37 1 0 0 0 0 23 26 1 1 0 0 0 23 27 1 0 0 0 0 24 29 1 0 0 0 0 24 34 2 0 0 0 0 24 36 1 0 0 0 0 25 30 1 1 0 0 0 26 4 1 1 0 0 0 27 29 1 1 0 0 0 28 19 1 6 0 0 0 29 30 1 1 0 0 0 30 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.31
Volume:	535.639
LogP:	2.362
LogD:	1.884
LogS:	-4.45
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	5.771
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.186
MDCK Permeability:	1.5352770788013004e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.559
Plasma Protein Binding (PPB):	89.05115509033203%
Volume Distribution (VD):	0.692
Pgp-substrate:	7.066824913024902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.797

ADMET: Excretion

Clearance (CL):	2.343
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.539
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.552
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.017
Carcinogencity:	0.923
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC90952

Natural Product ID:	NPC90952
*Common Name:**	Galphimine C
IUPAC Name:	n.a.
Synonyms:	Galphimine C
Standard InCHIKey:	KBMOWKVFQHQUFB-NHBPQBDCSA-N
Standard InCHI:	InChI=1S/C30H44O7/c1-18-9-10-25(3)11-13-27(5)23-20(32)16-28(19(2)31)17-37-22(33)8-7-21(28)26(23,4)12-14-29(27,24(34)36-6)30(25,35)15-18/h7-8,15,19-21,23,31-32,35H,9-14,16-17H2,1-6H3/t19-,20-,21+,23+,25-,26+,27-,28+,29+,30+/m1/s1
SMILES:	COC(=O)[C@@]12CC[C@@]3([C@@H]([C@@]1(C)CC[C@@]1([C@@]2(O)C=C(C)CC1)C)[C@H](O)C[C@@]1([C@H]3C=CC(=O)OC1)[C@H](O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463494
PubChem CID:	21578026
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids

*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
NPO19117	Galphimia glauca	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398543]
NPO19117	Galphimia glauca	Species	Malpighiaceae	Eukaryota	sedative extracts	n.a.	n.a.	PMID[15104495]
NPO19117	Galphimia glauca	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441069]
NPO19117	Galphimia glauca	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[538252]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[538252]
NPT5198	Cell Line	OVCAR	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[538252]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	4.0	ug ml-1	PMID[538252]

☑ 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 NPC90952 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	236
0.1-0.2	1362
0.2-0.3	3957
0.3-0.4	6745
0.4-0.5	12176
0.5-0.6	8715
0.6-0.7	5822
0.7-0.8	3433
0.8-0.85	214
0.85-0.9	30
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC277769
0.9619	High Similarity	NPC4573
0.9444	High Similarity	NPC134430
0.9273	High Similarity	NPC77689
0.9273	High Similarity	NPC473636
0.9266	High Similarity	NPC475809
0.9099	High Similarity	NPC473839
0.9099	High Similarity	NPC211093
0.8879	High Similarity	NPC275539
0.8879	High Similarity	NPC189075
0.8857	High Similarity	NPC478057
0.8857	High Similarity	NPC95899
0.8818	High Similarity	NPC25909
0.8785	High Similarity	NPC110496
0.875	High Similarity	NPC476959
0.8727	High Similarity	NPC269530
0.8684	High Similarity	NPC476962
0.8679	High Similarity	NPC90177
0.8667	High Similarity	NPC471412
0.8621	High Similarity	NPC469789
0.8585	High Similarity	NPC162973
0.8571	High Similarity	NPC471413
0.8571	High Similarity	NPC470953
0.8559	High Similarity	NPC194951
0.8559	High Similarity	NPC12046
0.8532	High Similarity	NPC476802
0.8532	High Similarity	NPC89171
0.8532	High Similarity	NPC473483
0.8505	High Similarity	NPC476889
0.8505	High Similarity	NPC254202
0.8482	Intermediate Similarity	NPC157441
0.8476	Intermediate Similarity	NPC316598
0.8475	Intermediate Similarity	NPC293112
0.8455	Intermediate Similarity	NPC31522
0.8448	Intermediate Similarity	NPC46570
0.8448	Intermediate Similarity	NPC67569
0.844	Intermediate Similarity	NPC475570
0.8435	Intermediate Similarity	NPC476960
0.8426	Intermediate Similarity	NPC475036
0.8426	Intermediate Similarity	NPC239162
0.8421	Intermediate Similarity	NPC469684
0.8421	Intermediate Similarity	NPC473968
0.8411	Intermediate Similarity	NPC476890
0.8411	Intermediate Similarity	NPC165250
0.8411	Intermediate Similarity	NPC40918
0.8411	Intermediate Similarity	NPC478156
0.8396	Intermediate Similarity	NPC471041
0.8396	Intermediate Similarity	NPC117685
0.8396	Intermediate Similarity	NPC474718
0.839	Intermediate Similarity	NPC81736
0.839	Intermediate Similarity	NPC470922
0.839	Intermediate Similarity	NPC8369
0.839	Intermediate Similarity	NPC172154
0.8376	Intermediate Similarity	NPC107493
0.8376	Intermediate Similarity	NPC470265
0.8376	Intermediate Similarity	NPC23786
0.8365	Intermediate Similarity	NPC266899
0.8364	Intermediate Similarity	NPC476765
0.8364	Intermediate Similarity	NPC90946
0.8364	Intermediate Similarity	NPC300614
0.8362	Intermediate Similarity	NPC476961
0.8349	Intermediate Similarity	NPC1679
0.8333	Intermediate Similarity	NPC268954
0.8333	Intermediate Similarity	NPC476963
0.8333	Intermediate Similarity	NPC469794
0.8333	Intermediate Similarity	NPC44170
0.8333	Intermediate Similarity	NPC282233
0.8333	Intermediate Similarity	NPC72772
0.8333	Intermediate Similarity	NPC95585
0.8319	Intermediate Similarity	NPC159333
0.8319	Intermediate Similarity	NPC122056
0.8318	Intermediate Similarity	NPC93744
0.8318	Intermediate Similarity	NPC476888
0.8305	Intermediate Similarity	NPC11895
0.8305	Intermediate Similarity	NPC67251
0.8305	Intermediate Similarity	NPC55602
0.8288	Intermediate Similarity	NPC476759
0.8288	Intermediate Similarity	NPC474243
0.8286	Intermediate Similarity	NPC234993
0.8286	Intermediate Similarity	NPC202833
0.8286	Intermediate Similarity	NPC242848
0.8286	Intermediate Similarity	NPC134072
0.8286	Intermediate Similarity	NPC29952
0.8273	Intermediate Similarity	NPC263729
0.8264	Intermediate Similarity	NPC231529
0.8257	Intermediate Similarity	NPC118911
0.8246	Intermediate Similarity	NPC110861
0.8246	Intermediate Similarity	NPC147912
0.8246	Intermediate Similarity	NPC67259
0.8241	Intermediate Similarity	NPC476081
0.8241	Intermediate Similarity	NPC475091
0.8235	Intermediate Similarity	NPC476729
0.823	Intermediate Similarity	NPC476801
0.8224	Intermediate Similarity	NPC476299
0.8224	Intermediate Similarity	NPC474012
0.8224	Intermediate Similarity	NPC476767
0.8224	Intermediate Similarity	NPC251680
0.822	Intermediate Similarity	NPC170538
0.822	Intermediate Similarity	NPC269642
0.8214	Intermediate Similarity	NPC476766
0.8214	Intermediate Similarity	NPC472666
0.8214	Intermediate Similarity	NPC5103
0.8208	Intermediate Similarity	NPC89225
0.8208	Intermediate Similarity	NPC473456
0.8208	Intermediate Similarity	NPC287668
0.8208	Intermediate Similarity	NPC189880
0.8205	Intermediate Similarity	NPC184555
0.8198	Intermediate Similarity	NPC322903
0.8198	Intermediate Similarity	NPC325054
0.819	Intermediate Similarity	NPC709
0.819	Intermediate Similarity	NPC251310
0.819	Intermediate Similarity	NPC50774
0.8182	Intermediate Similarity	NPC469607
0.8182	Intermediate Similarity	NPC112492
0.8182	Intermediate Similarity	NPC472269
0.8182	Intermediate Similarity	NPC284365
0.8182	Intermediate Similarity	NPC23020
0.8182	Intermediate Similarity	NPC472268
0.8182	Intermediate Similarity	NPC123726
0.8182	Intermediate Similarity	NPC472270
0.8174	Intermediate Similarity	NPC176840
0.8174	Intermediate Similarity	NPC470075
0.8174	Intermediate Similarity	NPC64318
0.8167	Intermediate Similarity	NPC473635
0.8165	Intermediate Similarity	NPC471208
0.8165	Intermediate Similarity	NPC112009
0.8158	Intermediate Similarity	NPC469463
0.8158	Intermediate Similarity	NPC469454
0.8158	Intermediate Similarity	NPC469496
0.8151	Intermediate Similarity	NPC105926
0.8151	Intermediate Similarity	NPC91693
0.8151	Intermediate Similarity	NPC204812
0.8151	Intermediate Similarity	NPC265557
0.8151	Intermediate Similarity	NPC18945
0.8148	Intermediate Similarity	NPC111292
0.8148	Intermediate Similarity	NPC235142
0.8142	Intermediate Similarity	NPC146945
0.8142	Intermediate Similarity	NPC171888
0.8142	Intermediate Similarity	NPC474315
0.8136	Intermediate Similarity	NPC470779
0.8131	Intermediate Similarity	NPC478056
0.8131	Intermediate Similarity	NPC325229
0.8131	Intermediate Similarity	NPC260149
0.8131	Intermediate Similarity	NPC174663
0.8131	Intermediate Similarity	NPC275086
0.8131	Intermediate Similarity	NPC58942
0.8125	Intermediate Similarity	NPC257082
0.8125	Intermediate Similarity	NPC112457
0.812	Intermediate Similarity	NPC475775
0.812	Intermediate Similarity	NPC475041
0.812	Intermediate Similarity	NPC476529
0.8115	Intermediate Similarity	NPC221414
0.8113	Intermediate Similarity	NPC472806
0.8113	Intermediate Similarity	NPC476327
0.8113	Intermediate Similarity	NPC167193
0.8113	Intermediate Similarity	NPC98874
0.8113	Intermediate Similarity	NPC476318
0.8108	Intermediate Similarity	NPC187435
0.8108	Intermediate Similarity	NPC67321
0.8103	Intermediate Similarity	NPC183580
0.8103	Intermediate Similarity	NPC470959
0.8103	Intermediate Similarity	NPC474483
0.8103	Intermediate Similarity	NPC476965
0.8103	Intermediate Similarity	NPC286528
0.8103	Intermediate Similarity	NPC312824
0.8103	Intermediate Similarity	NPC140055
0.8103	Intermediate Similarity	NPC239273
0.8103	Intermediate Similarity	NPC20302
0.8103	Intermediate Similarity	NPC55296
0.8103	Intermediate Similarity	NPC470493
0.8103	Intermediate Similarity	NPC167606
0.8103	Intermediate Similarity	NPC470492
0.8099	Intermediate Similarity	NPC287423
0.8095	Intermediate Similarity	NPC91010
0.8091	Intermediate Similarity	NPC296950
0.8091	Intermediate Similarity	NPC474281
0.8091	Intermediate Similarity	NPC201763
0.8091	Intermediate Similarity	NPC146731
0.8091	Intermediate Similarity	NPC470297
0.8087	Intermediate Similarity	NPC238667
0.8083	Intermediate Similarity	NPC24651
0.8083	Intermediate Similarity	NPC241456
0.8083	Intermediate Similarity	NPC8374
0.8083	Intermediate Similarity	NPC32868
0.8077	Intermediate Similarity	NPC472975
0.8077	Intermediate Similarity	NPC472978
0.8073	Intermediate Similarity	NPC136289
0.8073	Intermediate Similarity	NPC475038
0.8073	Intermediate Similarity	NPC476769
0.8073	Intermediate Similarity	NPC474709
0.8073	Intermediate Similarity	NPC109195
0.8073	Intermediate Similarity	NPC164551
0.8073	Intermediate Similarity	NPC295791
0.807	Intermediate Similarity	NPC234042
0.807	Intermediate Similarity	NPC152117
0.807	Intermediate Similarity	NPC470063
0.8067	Intermediate Similarity	NPC312833
0.8056	Intermediate Similarity	NPC47024
0.8056	Intermediate Similarity	NPC174314
0.8056	Intermediate Similarity	NPC54705

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 NPC90952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1563
0.2-0.3	3531
0.3-0.4	2372
0.4-0.5	916
0.5-0.6	314
0.6-0.7	163
0.7-0.8	80
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8224	Intermediate Similarity	NPD7640	Approved
0.8224	Intermediate Similarity	NPD7639	Approved
0.8131	Intermediate Similarity	NPD7638	Approved
0.8103	Intermediate Similarity	NPD7115	Discovery
0.7876	Intermediate Similarity	NPD6881	Approved
0.7876	Intermediate Similarity	NPD6899	Approved
0.7823	Intermediate Similarity	NPD7319	Approved
0.7788	Intermediate Similarity	NPD5697	Approved
0.7757	Intermediate Similarity	NPD7748	Approved
0.775	Intermediate Similarity	NPD6319	Approved
0.7742	Intermediate Similarity	NPD7736	Approved
0.7739	Intermediate Similarity	NPD6883	Approved
0.7739	Intermediate Similarity	NPD7102	Approved
0.7739	Intermediate Similarity	NPD7290	Approved
0.7736	Intermediate Similarity	NPD7515	Phase 2
0.7724	Intermediate Similarity	NPD7507	Approved
0.7719	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7902	Approved
0.7699	Intermediate Similarity	NPD6675	Approved
0.7699	Intermediate Similarity	NPD6402	Approved
0.7699	Intermediate Similarity	NPD7128	Approved
0.7699	Intermediate Similarity	NPD5739	Approved
0.7672	Intermediate Similarity	NPD6617	Approved
0.7672	Intermediate Similarity	NPD6650	Approved
0.7672	Intermediate Similarity	NPD6869	Approved
0.7672	Intermediate Similarity	NPD6847	Approved
0.7672	Intermediate Similarity	NPD6649	Approved
0.7672	Intermediate Similarity	NPD8130	Phase 1
0.7664	Intermediate Similarity	NPD5779	Approved
0.7664	Intermediate Similarity	NPD5778	Approved
0.7652	Intermediate Similarity	NPD6012	Approved
0.7652	Intermediate Similarity	NPD6014	Approved
0.7652	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD6013	Approved
0.7642	Intermediate Similarity	NPD7492	Approved
0.7636	Intermediate Similarity	NPD4225	Approved
0.7607	Intermediate Similarity	NPD6882	Approved
0.7607	Intermediate Similarity	NPD8297	Approved
0.7603	Intermediate Similarity	NPD6054	Approved
0.7589	Intermediate Similarity	NPD5211	Phase 2
0.7589	Intermediate Similarity	NPD7632	Discontinued
0.7581	Intermediate Similarity	NPD6616	Approved
0.7565	Intermediate Similarity	NPD7320	Approved
0.7565	Intermediate Similarity	NPD6011	Approved
0.7565	Intermediate Similarity	NPD6686	Approved
0.7561	Intermediate Similarity	NPD8328	Phase 3
0.7542	Intermediate Similarity	NPD4632	Approved
0.7524	Intermediate Similarity	NPD3573	Approved
0.752	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.748	Intermediate Similarity	NPD6370	Approved
0.7478	Intermediate Similarity	NPD5701	Approved
0.7458	Intermediate Similarity	NPD6053	Discontinued
0.7456	Intermediate Similarity	NPD5141	Approved
0.7436	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4634	Approved
0.7431	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7900	Approved
0.7411	Intermediate Similarity	NPD5285	Approved
0.7411	Intermediate Similarity	NPD5286	Approved
0.7411	Intermediate Similarity	NPD4696	Approved
0.7407	Intermediate Similarity	NPD6411	Approved
0.7407	Intermediate Similarity	NPD6079	Approved
0.7398	Intermediate Similarity	NPD6015	Approved
0.7398	Intermediate Similarity	NPD6016	Approved
0.7355	Intermediate Similarity	NPD6009	Approved
0.7339	Intermediate Similarity	NPD5988	Approved
0.7317	Intermediate Similarity	NPD6059	Approved
0.7281	Intermediate Similarity	NPD5225	Approved
0.7281	Intermediate Similarity	NPD4633	Approved
0.7281	Intermediate Similarity	NPD5224	Approved
0.7281	Intermediate Similarity	NPD5226	Approved
0.728	Intermediate Similarity	NPD7604	Phase 2
0.7258	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD8516	Approved
0.7258	Intermediate Similarity	NPD5983	Phase 2
0.7258	Intermediate Similarity	NPD8513	Phase 3
0.7258	Intermediate Similarity	NPD8515	Approved
0.7244	Intermediate Similarity	NPD8293	Discontinued
0.7241	Intermediate Similarity	NPD6008	Approved
0.7236	Intermediate Similarity	NPD7101	Approved
0.7236	Intermediate Similarity	NPD7100	Approved
0.7232	Intermediate Similarity	NPD4755	Approved
0.7227	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5328	Approved
0.7222	Intermediate Similarity	NPD6101	Approved
0.7217	Intermediate Similarity	NPD5174	Approved
0.7217	Intermediate Similarity	NPD5175	Approved
0.7213	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5223	Approved
0.7193	Intermediate Similarity	NPD5344	Discontinued
0.7179	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6336	Discontinued
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD6335	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD6371	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6274	Approved
0.712	Intermediate Similarity	NPD7503	Approved
0.7105	Intermediate Similarity	NPD4700	Approved
0.7097	Intermediate Similarity	NPD7516	Approved
0.708	Intermediate Similarity	NPD5173	Approved
0.708	Intermediate Similarity	NPD6084	Phase 2
0.708	Intermediate Similarity	NPD6083	Phase 2
0.7073	Intermediate Similarity	NPD6317	Approved
0.7048	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8294	Approved
0.704	Intermediate Similarity	NPD8377	Approved
0.7034	Intermediate Similarity	NPD6412	Phase 2
0.7027	Intermediate Similarity	NPD6399	Phase 3
0.7016	Intermediate Similarity	NPD6313	Approved
0.7016	Intermediate Similarity	NPD6314	Approved
0.7009	Intermediate Similarity	NPD1694	Approved
0.6992	Remote Similarity	NPD6868	Approved
0.6984	Remote Similarity	NPD8335	Approved
0.6984	Remote Similarity	NPD8378	Approved
0.6984	Remote Similarity	NPD8296	Approved
0.6984	Remote Similarity	NPD6921	Approved
0.6984	Remote Similarity	NPD8033	Approved
0.6984	Remote Similarity	NPD8380	Approved
0.6984	Remote Similarity	NPD8379	Approved
0.6975	Remote Similarity	NPD4729	Approved
0.6975	Remote Similarity	NPD4730	Approved
0.6972	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8133	Approved
0.6957	Remote Similarity	NPD6648	Approved
0.6944	Remote Similarity	NPD3618	Phase 1
0.6937	Remote Similarity	NPD8035	Phase 2
0.6937	Remote Similarity	NPD7983	Approved
0.6937	Remote Similarity	NPD7637	Suspended
0.6937	Remote Similarity	NPD8034	Phase 2
0.6917	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4202	Approved
0.686	Remote Similarity	NPD5250	Approved
0.686	Remote Similarity	NPD5247	Approved
0.686	Remote Similarity	NPD5251	Approved
0.686	Remote Similarity	NPD5248	Approved
0.686	Remote Similarity	NPD5249	Phase 3
0.6852	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6908	Approved
0.685	Remote Similarity	NPD6909	Approved
0.6847	Remote Similarity	NPD46	Approved
0.6847	Remote Similarity	NPD6698	Approved
0.6847	Remote Similarity	NPD5785	Approved
0.6846	Remote Similarity	NPD8074	Phase 3
0.6842	Remote Similarity	NPD4697	Phase 3
0.6833	Remote Similarity	NPD5128	Approved
0.6807	Remote Similarity	NPD4768	Approved
0.6807	Remote Similarity	NPD4767	Approved
0.6803	Remote Similarity	NPD5215	Approved
0.6803	Remote Similarity	NPD5216	Approved
0.6803	Remote Similarity	NPD5217	Approved
0.6794	Remote Similarity	NPD6033	Approved
0.6789	Remote Similarity	NPD6684	Approved
0.6789	Remote Similarity	NPD6409	Approved
0.6789	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7334	Approved
0.6789	Remote Similarity	NPD5330	Approved
0.6789	Remote Similarity	NPD7521	Approved
0.6789	Remote Similarity	NPD7146	Approved
0.678	Remote Similarity	NPD4754	Approved
0.6762	Remote Similarity	NPD7645	Phase 2
0.6754	Remote Similarity	NPD5695	Phase 3
0.675	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5696	Approved
0.6721	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5135	Approved
0.6721	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6642	Remote Similarity	NPD7260	Phase 2
0.6637	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD4623	Approved
0.6636	Remote Similarity	NPD4519	Discontinued
0.6609	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5210	Approved
0.6609	Remote Similarity	NPD4629	Approved
0.6607	Remote Similarity	NPD4753	Phase 2
0.6607	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3665	Phase 1
0.6606	Remote Similarity	NPD4786	Approved
0.6606	Remote Similarity	NPD3133	Approved
0.6606	Remote Similarity	NPD3666	Approved
0.6597	Remote Similarity	NPD7236	Approved
0.6594	Remote Similarity	NPD6334	Approved
0.6594	Remote Similarity	NPD6333	Approved
0.6581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3667	Approved
0.6557	Remote Similarity	NPD5168	Approved
0.6552	Remote Similarity	NPD7839	Suspended
0.6552	Remote Similarity	NPD7614	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