NPASS Compound

Structure

NPC475809 OpenBabel07101718182D 38 42 0 0 1 0 0 0 0 0999 V2000 -0.8267 -2.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4302 1.2149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1333 0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 2.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 -2.8636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0529 1.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9835 1.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 -0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 1.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4800 0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0529 3.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 -1.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8444 2.0750 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3066 1.9091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3977 2.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 2.8636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6533 1.9091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4800 3.3409 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8267 -1.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 0.4773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4800 1.4318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8267 1.4318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3066 2.8636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8267 0.4773 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 4.7962 2.1463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3523 2.3864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 3.3409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4800 4.2955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 -0.4773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 -1.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9835 3.2464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 18 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 6 37 1 0 0 0 0 7 8 2 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 17 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 17 1 0 0 0 0 15 30 1 0 0 0 0 16 28 1 0 0 0 0 16 38 1 0 0 0 0 18 31 1 0 0 0 0 19 26 1 1 0 0 0 19 28 1 0 0 0 0 20 32 2 0 0 0 0 20 38 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 33 1 6 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 28 1 6 0 0 0 23 34 1 0 0 0 0 24 29 1 0 0 0 0 24 35 2 0 0 0 0 24 37 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 18 1 6 0 0 0 29 30 1 1 0 0 0 30 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.3
Volume:	544.43
LogP:	1.924
LogD:	1.671
LogS:	-3.794
# Rotatable Bonds:	3
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	5.941
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:	-5.381
MDCK Permeability:	1.791098475223407e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.145
Human Intestinal Absorption (HIA):	0.147
20% Bioavailability (F20%):	0.588
30% Bioavailability (F30%):	0.348

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.777
Plasma Protein Binding (PPB):	68.5911636352539%
Volume Distribution (VD):	0.352
Pgp-substrate:	24.582937240600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.843
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	2.238
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.324
Human Hepatotoxicity (H-HT):	0.503
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.658
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.02
Carcinogencity:	0.725
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC475809

Natural Product ID:	NPC475809
*Common Name:**	Galphimine H
IUPAC Name:	n.a.
Synonyms:	Galphimine H
Standard InCHIKey:	IBYSPSUANRCDTF-HBOUEPRCSA-N
Standard InCHI:	InChI=1S/C30H44O8/c1-17-9-10-25(3)11-13-27(5)22-21(33)23(34)28(18(2)31)16-38-20(32)8-7-19(28)26(22,4)12-14-29(27,24(35)37-6)30(25,36)15-17/h7-8,18-19,21-23,31,33-34,36H,1,9-16H2,2-6H3/t18?,19-,21-,22-,23-,25+,26-,27+,28+,29-,30-/m0/s1
SMILES:	COC(=O)[C@@]12CC[C@@]3([C@@H]([C@@]1(C)CC[C@@]1([C@@]2(O)CC(=C)CC1)C)[C@H](O)[C@@H]([C@@]1([C@H]3C=CC(=O)OC1)C(O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516557
PubChem CID:	n.a.
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[457020]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[457020]
NPT5198	Cell Line	OVCAR	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[457020]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	4.0	ug ml-1	PMID[457020]

☑ 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 NPC475809 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	261
0.1-0.2	1487
0.2-0.3	3966
0.3-0.4	6719
0.4-0.5	11925
0.5-0.6	9241
0.6-0.7	5707
0.7-0.8	3022
0.8-0.85	336
0.85-0.9	24
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC473839
0.9817	High Similarity	NPC211093
0.9815	High Similarity	NPC134430
0.9636	High Similarity	NPC473636
0.9636	High Similarity	NPC77689
0.9626	High Similarity	NPC4573
0.9444	High Similarity	NPC277769
0.9266	High Similarity	NPC90952
0.8796	High Similarity	NPC475036
0.8609	High Similarity	NPC473968
0.8595	High Similarity	NPC231529
0.8584	High Similarity	NPC269530
0.8571	High Similarity	NPC470922
0.8559	High Similarity	NPC275539
0.8559	High Similarity	NPC189075
0.8559	High Similarity	NPC475263
0.8547	High Similarity	NPC476961
0.8522	High Similarity	NPC268954
0.8509	High Similarity	NPC25909
0.85	High Similarity	NPC293112
0.85	High Similarity	NPC473635
0.8487	Intermediate Similarity	NPC469789
0.8487	Intermediate Similarity	NPC67251
0.8487	Intermediate Similarity	NPC11895
0.8475	Intermediate Similarity	NPC470779
0.8468	Intermediate Similarity	NPC110496
0.8468	Intermediate Similarity	NPC473586
0.8462	Intermediate Similarity	NPC476529
0.8462	Intermediate Similarity	NPC475775
0.8448	Intermediate Similarity	NPC55296
0.8448	Intermediate Similarity	NPC476959
0.844	Intermediate Similarity	NPC474709
0.8435	Intermediate Similarity	NPC110861
0.8421	Intermediate Similarity	NPC476801
0.8417	Intermediate Similarity	NPC24651
0.8417	Intermediate Similarity	NPC81736
0.8417	Intermediate Similarity	NPC172154
0.8403	Intermediate Similarity	NPC269642
0.8403	Intermediate Similarity	NPC470265
0.8403	Intermediate Similarity	NPC23786
0.8403	Intermediate Similarity	NPC170538
0.839	Intermediate Similarity	NPC107338
0.839	Intermediate Similarity	NPC109607
0.839	Intermediate Similarity	NPC251226
0.8378	Intermediate Similarity	NPC88349
0.8376	Intermediate Similarity	NPC251310
0.8374	Intermediate Similarity	NPC477197
0.8364	Intermediate Similarity	NPC95899
0.8362	Intermediate Similarity	NPC470075
0.8362	Intermediate Similarity	NPC44170
0.8349	Intermediate Similarity	NPC471412
0.8348	Intermediate Similarity	NPC7921
0.8348	Intermediate Similarity	NPC208998
0.8333	Intermediate Similarity	NPC171888
0.8333	Intermediate Similarity	NPC265557
0.8333	Intermediate Similarity	NPC105926
0.8333	Intermediate Similarity	NPC18945
0.8333	Intermediate Similarity	NPC91693
0.8333	Intermediate Similarity	NPC146945
0.8319	Intermediate Similarity	NPC46570
0.8319	Intermediate Similarity	NPC67569
0.8319	Intermediate Similarity	NPC4021
0.8319	Intermediate Similarity	NPC159456
0.8293	Intermediate Similarity	NPC477196
0.8293	Intermediate Similarity	NPC477079
0.8293	Intermediate Similarity	NPC470913
0.8293	Intermediate Similarity	NPC477076
0.8293	Intermediate Similarity	NPC477077
0.8291	Intermediate Similarity	NPC476965
0.8291	Intermediate Similarity	NPC58662
0.8291	Intermediate Similarity	NPC470959
0.8291	Intermediate Similarity	NPC469684
0.8291	Intermediate Similarity	NPC474483
0.8291	Intermediate Similarity	NPC473590
0.8276	Intermediate Similarity	NPC147912
0.8276	Intermediate Similarity	NPC67259
0.8273	Intermediate Similarity	NPC273668
0.8273	Intermediate Similarity	NPC162973
0.8264	Intermediate Similarity	NPC476729
0.8264	Intermediate Similarity	NPC8369
0.8261	Intermediate Similarity	NPC12046
0.8261	Intermediate Similarity	NPC470063
0.8261	Intermediate Similarity	NPC194951
0.8257	Intermediate Similarity	NPC471413
0.825	Intermediate Similarity	NPC312833
0.825	Intermediate Similarity	NPC107493
0.824	Intermediate Similarity	NPC225791
0.824	Intermediate Similarity	NPC478151
0.8235	Intermediate Similarity	NPC268530
0.8235	Intermediate Similarity	NPC154491
0.823	Intermediate Similarity	NPC476802
0.823	Intermediate Similarity	NPC89171
0.823	Intermediate Similarity	NPC293850
0.822	Intermediate Similarity	NPC297179
0.822	Intermediate Similarity	NPC284707
0.8214	Intermediate Similarity	NPC477877
0.8211	Intermediate Similarity	NPC472270
0.8211	Intermediate Similarity	NPC472269
0.8211	Intermediate Similarity	NPC475281
0.8211	Intermediate Similarity	NPC23020
0.8211	Intermediate Similarity	NPC112492
0.8211	Intermediate Similarity	NPC477078
0.8211	Intermediate Similarity	NPC477075
0.8211	Intermediate Similarity	NPC472268
0.8211	Intermediate Similarity	NPC477193
0.8211	Intermediate Similarity	NPC329923
0.8211	Intermediate Similarity	NPC477194
0.8211	Intermediate Similarity	NPC477191
0.8211	Intermediate Similarity	NPC477192
0.8205	Intermediate Similarity	NPC64318
0.8205	Intermediate Similarity	NPC89929
0.8205	Intermediate Similarity	NPC471816
0.8198	Intermediate Similarity	NPC254202
0.8198	Intermediate Similarity	NPC478057
0.8198	Intermediate Similarity	NPC225238
0.8198	Intermediate Similarity	NPC476889
0.8198	Intermediate Similarity	NPC90177
0.819	Intermediate Similarity	NPC157441
0.819	Intermediate Similarity	NPC477126
0.819	Intermediate Similarity	NPC159333
0.819	Intermediate Similarity	NPC471204
0.819	Intermediate Similarity	NPC478212
0.8182	Intermediate Similarity	NPC55602
0.8182	Intermediate Similarity	NPC473979
0.8174	Intermediate Similarity	NPC469655
0.8174	Intermediate Similarity	NPC470076
0.8174	Intermediate Similarity	NPC469656
0.8174	Intermediate Similarity	NPC474846
0.8165	Intermediate Similarity	NPC316598
0.816	Intermediate Similarity	NPC312650
0.816	Intermediate Similarity	NPC478152
0.816	Intermediate Similarity	NPC476776
0.816	Intermediate Similarity	NPC192765
0.816	Intermediate Similarity	NPC478154
0.816	Intermediate Similarity	NPC277212
0.816	Intermediate Similarity	NPC477195
0.816	Intermediate Similarity	NPC71391
0.816	Intermediate Similarity	NPC478153
0.816	Intermediate Similarity	NPC178264
0.816	Intermediate Similarity	NPC46823
0.816	Intermediate Similarity	NPC30279
0.816	Intermediate Similarity	NPC478150
0.816	Intermediate Similarity	NPC473918
0.8158	Intermediate Similarity	NPC474243
0.8158	Intermediate Similarity	NPC310546
0.8151	Intermediate Similarity	NPC5292
0.8151	Intermediate Similarity	NPC469488
0.8151	Intermediate Similarity	NPC472667
0.8151	Intermediate Similarity	NPC42673
0.8151	Intermediate Similarity	NPC469380
0.8151	Intermediate Similarity	NPC230513
0.8151	Intermediate Similarity	NPC476960
0.8151	Intermediate Similarity	NPC475041
0.8145	Intermediate Similarity	NPC97918
0.8145	Intermediate Similarity	NPC115656
0.8145	Intermediate Similarity	NPC221414
0.8145	Intermediate Similarity	NPC82380
0.8145	Intermediate Similarity	NPC88311
0.8145	Intermediate Similarity	NPC280029
0.8145	Intermediate Similarity	NPC470518
0.8145	Intermediate Similarity	NPC244296
0.8145	Intermediate Similarity	NPC252289
0.8145	Intermediate Similarity	NPC305793
0.8145	Intermediate Similarity	NPC1314
0.8145	Intermediate Similarity	NPC269484
0.8145	Intermediate Similarity	NPC252657
0.8145	Intermediate Similarity	NPC11577
0.8145	Intermediate Similarity	NPC273878
0.8145	Intermediate Similarity	NPC9470
0.8145	Intermediate Similarity	NPC107536
0.8145	Intermediate Similarity	NPC470912
0.8145	Intermediate Similarity	NPC141600
0.8145	Intermediate Similarity	NPC476966
0.8145	Intermediate Similarity	NPC472267
0.8142	Intermediate Similarity	NPC187435
0.8142	Intermediate Similarity	NPC67321
0.8142	Intermediate Similarity	NPC301666
0.8136	Intermediate Similarity	NPC287343
0.8136	Intermediate Similarity	NPC176513
0.8136	Intermediate Similarity	NPC97908
0.8136	Intermediate Similarity	NPC98249
0.8136	Intermediate Similarity	NPC470775
0.8136	Intermediate Similarity	NPC122033
0.8136	Intermediate Similarity	NPC474654
0.8136	Intermediate Similarity	NPC53396
0.8136	Intermediate Similarity	NPC470854
0.8136	Intermediate Similarity	NPC470778
0.8136	Intermediate Similarity	NPC146432
0.813	Intermediate Similarity	NPC146456
0.813	Intermediate Similarity	NPC470516
0.813	Intermediate Similarity	NPC470882
0.813	Intermediate Similarity	NPC469757
0.813	Intermediate Similarity	NPC117702
0.813	Intermediate Similarity	NPC298841
0.813	Intermediate Similarity	NPC471357
0.812	Intermediate Similarity	NPC470953
0.8115	Intermediate Similarity	NPC469790
0.811	Intermediate Similarity	NPC110700
0.811	Intermediate Similarity	NPC279915
0.8108	Intermediate Similarity	NPC476081

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 NPC475809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1648
0.2-0.3	3513
0.3-0.4	2296
0.4-0.5	908
0.5-0.6	327
0.6-0.7	172
0.7-0.8	47
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD7319	Approved
0.7983	Intermediate Similarity	NPD7115	Discovery
0.7913	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD7507	Approved
0.7838	Intermediate Similarity	NPD7638	Approved
0.7787	Intermediate Similarity	NPD6319	Approved
0.7768	Intermediate Similarity	NPD7640	Approved
0.7768	Intermediate Similarity	NPD7639	Approved
0.7759	Intermediate Similarity	NPD6686	Approved
0.7742	Intermediate Similarity	NPD8328	Phase 3
0.7692	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4225	Approved
0.7541	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7479	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7748	Approved
0.7458	Intermediate Similarity	NPD6899	Approved
0.7458	Intermediate Similarity	NPD6881	Approved
0.7455	Intermediate Similarity	NPD7515	Phase 2
0.7438	Intermediate Similarity	NPD4632	Approved
0.7434	Intermediate Similarity	NPD7902	Approved
0.7419	Intermediate Similarity	NPD7516	Approved
0.7417	Intermediate Similarity	NPD6650	Approved
0.7417	Intermediate Similarity	NPD6649	Approved
0.7402	Intermediate Similarity	NPD7492	Approved
0.7391	Intermediate Similarity	NPD5344	Discontinued
0.7373	Intermediate Similarity	NPD5697	Approved
0.736	Intermediate Similarity	NPD6054	Approved
0.7355	Intermediate Similarity	NPD6882	Approved
0.7344	Intermediate Similarity	NPD6616	Approved
0.7339	Intermediate Similarity	NPD7328	Approved
0.7339	Intermediate Similarity	NPD7327	Approved
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD4634	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7302	Intermediate Similarity	NPD6921	Approved
0.7302	Intermediate Similarity	NPD8513	Phase 3
0.7302	Intermediate Similarity	NPD8515	Approved
0.7302	Intermediate Similarity	NPD8033	Approved
0.7302	Intermediate Similarity	NPD8516	Approved
0.7302	Intermediate Similarity	NPD8517	Approved
0.7288	Intermediate Similarity	NPD5739	Approved
0.7288	Intermediate Similarity	NPD6675	Approved
0.7288	Intermediate Similarity	NPD6402	Approved
0.7288	Intermediate Similarity	NPD7128	Approved
0.7287	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD6847	Approved
0.7273	Intermediate Similarity	NPD8130	Phase 1
0.725	Intermediate Similarity	NPD6373	Approved
0.725	Intermediate Similarity	NPD6014	Approved
0.725	Intermediate Similarity	NPD6013	Approved
0.725	Intermediate Similarity	NPD6372	Approved
0.725	Intermediate Similarity	NPD6012	Approved
0.7244	Intermediate Similarity	NPD6370	Approved
0.7232	Intermediate Similarity	NPD5778	Approved
0.7232	Intermediate Similarity	NPD5779	Approved
0.7227	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8377	Approved
0.7222	Intermediate Similarity	NPD8294	Approved
0.7213	Intermediate Similarity	NPD6053	Discontinued
0.7207	Intermediate Similarity	NPD46	Approved
0.7207	Intermediate Similarity	NPD6698	Approved
0.719	Intermediate Similarity	NPD6371	Approved
0.7179	Intermediate Similarity	NPD7632	Discontinued
0.7168	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7900	Approved
0.7167	Intermediate Similarity	NPD7320	Approved
0.7167	Intermediate Similarity	NPD6011	Approved
0.7165	Intermediate Similarity	NPD8296	Approved
0.7165	Intermediate Similarity	NPD8380	Approved
0.7165	Intermediate Similarity	NPD8335	Approved
0.7165	Intermediate Similarity	NPD7503	Approved
0.7165	Intermediate Similarity	NPD6016	Approved
0.7165	Intermediate Similarity	NPD8379	Approved
0.7165	Intermediate Similarity	NPD6015	Approved
0.7165	Intermediate Similarity	NPD8378	Approved
0.7154	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD7983	Approved
0.712	Intermediate Similarity	NPD6009	Approved
0.7109	Intermediate Similarity	NPD5988	Approved
0.7107	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3573	Approved
0.7087	Intermediate Similarity	NPD6059	Approved
0.7083	Intermediate Similarity	NPD5701	Approved
0.7083	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7604	Phase 2
0.7034	Intermediate Similarity	NPD5211	Phase 2
0.7031	Intermediate Similarity	NPD5983	Phase 2
0.7023	Intermediate Similarity	NPD8293	Discontinued
0.7009	Intermediate Similarity	NPD6648	Approved
0.7009	Intermediate Similarity	NPD5286	Approved
0.7009	Intermediate Similarity	NPD4696	Approved
0.7009	Intermediate Similarity	NPD5285	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.6991	Remote Similarity	NPD6079	Approved
0.6964	Remote Similarity	NPD6101	Approved
0.6964	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6336	Discontinued
0.6942	Remote Similarity	NPD6412	Phase 2
0.6917	Remote Similarity	NPD5141	Approved
0.6903	Remote Similarity	NPD7838	Discovery
0.6894	Remote Similarity	NPD8074	Phase 3
0.6891	Remote Similarity	NPD4633	Approved
0.6891	Remote Similarity	NPD5226	Approved
0.6891	Remote Similarity	NPD5225	Approved
0.6891	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD7100	Approved
0.6875	Remote Similarity	NPD7101	Approved
0.6855	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8035	Phase 2
0.6842	Remote Similarity	NPD8034	Phase 2
0.6838	Remote Similarity	NPD4755	Approved
0.6833	Remote Similarity	NPD5174	Approved
0.6833	Remote Similarity	NPD5175	Approved
0.6814	Remote Similarity	NPD5328	Approved
0.6807	Remote Similarity	NPD5223	Approved
0.6797	Remote Similarity	NPD6335	Approved
0.6789	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6399	Phase 3
0.6772	Remote Similarity	NPD6274	Approved
0.6757	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5221	Approved
0.6752	Remote Similarity	NPD5222	Approved
0.6748	Remote Similarity	NPD4729	Approved
0.6748	Remote Similarity	NPD4730	Approved
0.6723	Remote Similarity	NPD4700	Approved
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD7637	Suspended
0.6695	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6084	Phase 2
0.6695	Remote Similarity	NPD5173	Approved
0.6691	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD6868	Approved
0.664	Remote Similarity	NPD5248	Approved
0.664	Remote Similarity	NPD5251	Approved
0.664	Remote Similarity	NPD5250	Approved
0.664	Remote Similarity	NPD5247	Approved
0.664	Remote Similarity	NPD5249	Phase 3
0.6639	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5785	Approved
0.6607	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD6033	Approved
0.6585	Remote Similarity	NPD4767	Approved
0.6585	Remote Similarity	NPD4768	Approved
0.6579	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3618	Phase 1
0.6515	Remote Similarity	NPD6908	Approved
0.6515	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6909	Approved
0.6514	Remote Similarity	NPD7645	Phase 2
0.6496	Remote Similarity	NPD4202	Approved
0.648	Remote Similarity	NPD5128	Approved
0.6471	Remote Similarity	NPD7839	Suspended
0.6471	Remote Similarity	NPD4697	Phase 3
0.6457	Remote Similarity	NPD5216	Approved
0.6457	Remote Similarity	NPD5217	Approved
0.6457	Remote Similarity	NPD5215	Approved
0.6441	Remote Similarity	NPD5282	Discontinued
0.6423	Remote Similarity	NPD4754	Approved
0.6419	Remote Similarity	NPD7236	Approved
0.6418	Remote Similarity	NPD7829	Approved
0.6418	Remote Similarity	NPD7830	Approved
0.6404	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD6684	Approved
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD5330	Approved
0.6387	Remote Similarity	NPD5695	Phase 3
0.6379	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5169	Approved
0.6378	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5135	Approved
0.6372	Remote Similarity	NPD4786	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD3667	Approved
0.6338	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5127	Approved
0.6316	Remote Similarity	NPD7239	Suspended
0.6306	Remote Similarity	NPD7525	Registered
0.6296	Remote Similarity	NPD7642	Approved
0.6296	Remote Similarity	NPD7799	Discontinued
0.6294	Remote Similarity	NPD6333	Approved
0.6294	Remote Similarity	NPD6334	Approved
0.6293	Remote Similarity	NPD5737	Approved
0.6293	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD6903	Approved
0.6286	Remote Similarity	NPD6845	Suspended
0.6271	Remote Similarity	NPD5693	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