NPASS Compound

Structure

NPC61688 OpenBabel07101719252D 31 35 0 0 1 0 0 0 0 0999 V2000 -3.9703 -3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 -5.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 -4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -3.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6320 -5.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9629 -6.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.5000 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 2 17 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 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 12 1 0 0 0 0 11 24 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 26 1 0 0 0 0 15 31 1 0 0 0 0 16 1 1 1 0 0 0 16 18 1 0 0 0 0 17 28 2 0 0 0 0 18 24 1 1 0 0 0 19 22 1 0 0 0 0 19 29 2 0 0 0 0 20 26 1 1 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 1 0 0 0 22 25 1 6 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 1 0 0 0 25 6 1 6 0 0 0 26 12 1 1 0 0 0 27 14 1 6 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.31
Volume:	462.654
LogP:	3.72
LogD:	3.944
LogS:	-4.472
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	6.263
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	1.7672995454631746e-05
Pgp-inhibitor:	0.732
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.837
Plasma Protein Binding (PPB):	73.27753448486328%
Volume Distribution (VD):	1.068
Pgp-substrate:	11.251470565795898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.665
CYP3A4-inhibitor:	0.797
CYP3A4-substrate:	0.638

ADMET: Excretion

Clearance (CL):	7.266
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.312
Drug-inuced Liver Injury (DILI):	0.195
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.381
Carcinogencity:	0.161
Eye Corrosion:	0.02
Eye Irritation:	0.074
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC61688

Natural Product ID:	NPC61688
*Common Name:**	FGMDCYOFHYPQLK-BDLUGEFISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FGMDCYOFHYPQLK-BDLUGEFISA-N
Standard InCHI:	InChI=1S/C27H42O4/c1-16(13-17(2)28)18-9-10-25(6)22-19(29)14-27-20(7-8-21(30)23(27,3)4)26(22,15-31-27)12-11-24(18,25)5/h16,18,20-22,30H,7-15H2,1-6H3/t16-,18-,20+,21+,22+,24-,25+,26-,27-/m1/s1
SMILES:	CC(=O)C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2C(=O)C[C@]2([C@H]3CC[C@@H](C2(C)C)O)OC1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3264666
PubChem CID:	24814301
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17685651]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[18637688]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24836069]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621938]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Vines	n.a.	n.a.	PMID[32357011]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8182	Momordica charantia	Species	Cucurbitaceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	-49.0	%	PMID[456150]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	-39.0	%	PMID[456150]

☑ 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 NPC61688 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	394
0.1-0.2	3365
0.2-0.3	8744
0.3-0.4	14089
0.4-0.5	6130
0.5-0.6	5733
0.6-0.7	3206
0.7-0.8	903
0.8-0.85	93
0.85-0.9	35
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9186	High Similarity	NPC477614
0.9186	High Similarity	NPC226491
0.9167	High Similarity	NPC50438
0.8953	High Similarity	NPC80700
0.8851	High Similarity	NPC263802
0.8837	High Similarity	NPC473350
0.8791	High Similarity	NPC62407
0.8791	High Similarity	NPC287354
0.8778	High Similarity	NPC476189
0.8721	High Similarity	NPC473336
0.8721	High Similarity	NPC471044
0.8721	High Similarity	NPC477434
0.8696	High Similarity	NPC116683
0.8652	High Similarity	NPC200580
0.8605	High Similarity	NPC268578
0.8605	High Similarity	NPC217559
0.8605	High Similarity	NPC292458
0.8587	High Similarity	NPC17336
0.8556	High Similarity	NPC476296
0.8523	High Similarity	NPC302111
0.8523	High Similarity	NPC83242
0.8495	Intermediate Similarity	NPC193785
0.8444	Intermediate Similarity	NPC24705
0.8444	Intermediate Similarity	NPC67653
0.8444	Intermediate Similarity	NPC471459
0.8444	Intermediate Similarity	NPC56962
0.8434	Intermediate Similarity	NPC472487
0.8434	Intermediate Similarity	NPC472486
0.8404	Intermediate Similarity	NPC111187
0.8404	Intermediate Similarity	NPC190080
0.8372	Intermediate Similarity	NPC58631
0.837	Intermediate Similarity	NPC161035
0.8333	Intermediate Similarity	NPC178853
0.8316	Intermediate Similarity	NPC476294
0.8313	Intermediate Similarity	NPC159789
0.8313	Intermediate Similarity	NPC125767
0.8313	Intermediate Similarity	NPC21220
0.8298	Intermediate Similarity	NPC476728
0.8295	Intermediate Similarity	NPC237938
0.8295	Intermediate Similarity	NPC219535
0.8295	Intermediate Similarity	NPC34984
0.8295	Intermediate Similarity	NPC25037
0.828	Intermediate Similarity	NPC470424
0.8276	Intermediate Similarity	NPC13494
0.8276	Intermediate Similarity	NPC268040
0.8276	Intermediate Similarity	NPC317066
0.8265	Intermediate Similarity	NPC88469
0.8247	Intermediate Similarity	NPC124544
0.8242	Intermediate Similarity	NPC477443
0.8242	Intermediate Similarity	NPC477440
0.8211	Intermediate Similarity	NPC253586
0.8202	Intermediate Similarity	NPC477205
0.8202	Intermediate Similarity	NPC477445
0.8191	Intermediate Similarity	NPC305808
0.8182	Intermediate Similarity	NPC327451
0.8161	Intermediate Similarity	NPC50658
0.8152	Intermediate Similarity	NPC475211
0.8152	Intermediate Similarity	NPC477433
0.8152	Intermediate Similarity	NPC477442
0.8152	Intermediate Similarity	NPC88337
0.8152	Intermediate Similarity	NPC477444
0.8144	Intermediate Similarity	NPC46848
0.814	Intermediate Similarity	NPC31302
0.814	Intermediate Similarity	NPC80891
0.814	Intermediate Similarity	NPC320144
0.814	Intermediate Similarity	NPC245029
0.814	Intermediate Similarity	NPC201276
0.8132	Intermediate Similarity	NPC471221
0.8132	Intermediate Similarity	NPC476435
0.8132	Intermediate Similarity	NPC473319
0.8132	Intermediate Similarity	NPC3032
0.8132	Intermediate Similarity	NPC131104
0.8118	Intermediate Similarity	NPC221420
0.8118	Intermediate Similarity	NPC23884
0.8111	Intermediate Similarity	NPC476727
0.8111	Intermediate Similarity	NPC476726
0.8111	Intermediate Similarity	NPC474448
0.8105	Intermediate Similarity	NPC163685
0.809	Intermediate Similarity	NPC475689
0.809	Intermediate Similarity	NPC319909
0.809	Intermediate Similarity	NPC474996
0.809	Intermediate Similarity	NPC473299
0.8081	Intermediate Similarity	NPC327093
0.8072	Intermediate Similarity	NPC232112
0.8068	Intermediate Similarity	NPC289486
0.8068	Intermediate Similarity	NPC61107
0.8065	Intermediate Similarity	NPC475878
0.8065	Intermediate Similarity	NPC52756
0.8061	Intermediate Similarity	NPC213528
0.8061	Intermediate Similarity	NPC246736
0.8061	Intermediate Similarity	NPC76866
0.8061	Intermediate Similarity	NPC214946
0.8061	Intermediate Similarity	NPC148628
0.8061	Intermediate Similarity	NPC244969
0.8061	Intermediate Similarity	NPC304832
0.8061	Intermediate Similarity	NPC88203
0.8061	Intermediate Similarity	NPC275990
0.8061	Intermediate Similarity	NPC286519
0.8061	Intermediate Similarity	NPC471254
0.8046	Intermediate Similarity	NPC470609
0.8041	Intermediate Similarity	NPC108371
0.8041	Intermediate Similarity	NPC94906
0.8023	Intermediate Similarity	NPC185465
0.8023	Intermediate Similarity	NPC80089
0.8023	Intermediate Similarity	NPC34046
0.8023	Intermediate Similarity	NPC171426
0.8023	Intermediate Similarity	NPC324700
0.8023	Intermediate Similarity	NPC224802
0.8022	Intermediate Similarity	NPC202937
0.8021	Intermediate Similarity	NPC170978
0.8	Intermediate Similarity	NPC82633
0.8	Intermediate Similarity	NPC475742
0.8	Intermediate Similarity	NPC5767
0.798	Intermediate Similarity	NPC34562
0.7978	Intermediate Similarity	NPC15091
0.7961	Intermediate Similarity	NPC473062
0.7959	Intermediate Similarity	NPC52899
0.7959	Intermediate Similarity	NPC163963
0.7959	Intermediate Similarity	NPC289148
0.7957	Intermediate Similarity	NPC470114
0.7957	Intermediate Similarity	NPC77756
0.7957	Intermediate Similarity	NPC46758
0.7955	Intermediate Similarity	NPC469745
0.7955	Intermediate Similarity	NPC254123
0.7952	Intermediate Similarity	NPC320549
0.7952	Intermediate Similarity	NPC156277
0.7952	Intermediate Similarity	NPC151018
0.7952	Intermediate Similarity	NPC58057
0.7952	Intermediate Similarity	NPC89310
0.7938	Intermediate Similarity	NPC472144
0.7938	Intermediate Similarity	NPC20479
0.7938	Intermediate Similarity	NPC472028
0.7938	Intermediate Similarity	NPC38296
0.7938	Intermediate Similarity	NPC162459
0.7938	Intermediate Similarity	NPC471038
0.7938	Intermediate Similarity	NPC38471
0.7938	Intermediate Similarity	NPC253995
0.7938	Intermediate Similarity	NPC98837
0.7938	Intermediate Similarity	NPC28864
0.7935	Intermediate Similarity	NPC90676
0.7931	Intermediate Similarity	NPC81074
0.7931	Intermediate Similarity	NPC477282
0.7917	Intermediate Similarity	NPC329910
0.7917	Intermediate Similarity	NPC477264
0.7917	Intermediate Similarity	NPC235109
0.7912	Intermediate Similarity	NPC475729
0.7912	Intermediate Similarity	NPC92139
0.7912	Intermediate Similarity	NPC472272
0.7912	Intermediate Similarity	NPC155531
0.7912	Intermediate Similarity	NPC215968
0.7912	Intermediate Similarity	NPC474215
0.7912	Intermediate Similarity	NPC114378
0.7912	Intermediate Similarity	NPC103782
0.7912	Intermediate Similarity	NPC472745
0.7907	Intermediate Similarity	NPC477918
0.7907	Intermediate Similarity	NPC11907
0.7907	Intermediate Similarity	NPC475031
0.7907	Intermediate Similarity	NPC133596
0.79	Intermediate Similarity	NPC13149
0.79	Intermediate Similarity	NPC100078
0.7895	Intermediate Similarity	NPC215271
0.7895	Intermediate Similarity	NPC477495
0.7895	Intermediate Similarity	NPC104371
0.7895	Intermediate Similarity	NPC29247
0.7895	Intermediate Similarity	NPC91772
0.7895	Intermediate Similarity	NPC129004
0.7895	Intermediate Similarity	NPC292374
0.7895	Intermediate Similarity	NPC289539
0.7895	Intermediate Similarity	NPC111524
0.7895	Intermediate Similarity	NPC101233
0.7895	Intermediate Similarity	NPC261333
0.7895	Intermediate Similarity	NPC153775
0.7889	Intermediate Similarity	NPC105895
0.7882	Intermediate Similarity	NPC273366
0.7882	Intermediate Similarity	NPC97534
0.7882	Intermediate Similarity	NPC195155
0.7882	Intermediate Similarity	NPC174964
0.7879	Intermediate Similarity	NPC470172
0.7865	Intermediate Similarity	NPC328007
0.7857	Intermediate Similarity	NPC180733
0.7857	Intermediate Similarity	NPC293866
0.7857	Intermediate Similarity	NPC41971
0.7857	Intermediate Similarity	NPC37047
0.7857	Intermediate Similarity	NPC287676
0.7841	Intermediate Similarity	NPC477851
0.7835	Intermediate Similarity	NPC472145
0.7835	Intermediate Similarity	NPC469810
0.7826	Intermediate Similarity	NPC239938
0.7822	Intermediate Similarity	NPC37600
0.7822	Intermediate Similarity	NPC200957
0.7822	Intermediate Similarity	NPC138908
0.7822	Intermediate Similarity	NPC166079
0.7822	Intermediate Similarity	NPC4115
0.7822	Intermediate Similarity	NPC306776
0.7822	Intermediate Similarity	NPC295366
0.7816	Intermediate Similarity	NPC475725
0.7812	Intermediate Similarity	NPC470232
0.7812	Intermediate Similarity	NPC288906
0.7812	Intermediate Similarity	NPC470229
0.7812	Intermediate Similarity	NPC263135

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 NPC61688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	3636
0.2-0.3	3433
0.3-0.4	1018
0.4-0.5	261
0.5-0.6	219
0.6-0.7	126
0.7-0.8	29
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
0.8313	Intermediate Similarity	NPD3703	Phase 2
0.8023	Intermediate Similarity	NPD6118	Approved
0.8023	Intermediate Similarity	NPD6697	Approved
0.8023	Intermediate Similarity	NPD6115	Approved
0.8023	Intermediate Similarity	NPD6114	Approved
0.7952	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6117	Approved
0.7711	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6116	Phase 1
0.759	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5360	Phase 3
0.7558	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1700	Approved
0.7412	Intermediate Similarity	NPD4789	Approved
0.7412	Intermediate Similarity	NPD4244	Approved
0.7412	Intermediate Similarity	NPD4245	Approved
0.7294	Intermediate Similarity	NPD3698	Phase 2
0.7294	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4758	Discontinued
0.708	Intermediate Similarity	NPD6059	Approved
0.708	Intermediate Similarity	NPD6054	Approved
0.7079	Intermediate Similarity	NPD3702	Approved
0.7065	Intermediate Similarity	NPD6928	Phase 2
0.7033	Intermediate Similarity	NPD3671	Phase 1
0.7033	Intermediate Similarity	NPD5364	Discontinued
0.697	Remote Similarity	NPD8035	Phase 2
0.697	Remote Similarity	NPD8034	Phase 2
0.6957	Remote Similarity	NPD6370	Approved
0.6939	Remote Similarity	NPD5328	Approved
0.6932	Remote Similarity	NPD5777	Approved
0.6932	Remote Similarity	NPD6081	Approved
0.6875	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6016	Approved
0.687	Remote Similarity	NPD6015	Approved
0.6852	Remote Similarity	NPD7320	Approved
0.6838	Remote Similarity	NPD7492	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6822	Remote Similarity	NPD6008	Approved
0.681	Remote Similarity	NPD5988	Approved
0.6807	Remote Similarity	NPD7736	Approved
0.68	Remote Similarity	NPD6079	Approved
0.6796	Remote Similarity	NPD4755	Approved
0.6789	Remote Similarity	NPD6373	Approved
0.6789	Remote Similarity	NPD6372	Approved
0.678	Remote Similarity	NPD6616	Approved
0.6744	Remote Similarity	NPD4224	Phase 2
0.6727	Remote Similarity	NPD4634	Approved
0.6723	Remote Similarity	NPD8293	Discontinued
0.6723	Remote Similarity	NPD7078	Approved
0.6699	Remote Similarity	NPD4697	Phase 3
0.6697	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6638	Remote Similarity	NPD6319	Approved
0.6633	Remote Similarity	NPD3618	Phase 1
0.6629	Remote Similarity	NPD4787	Phase 1
0.6612	Remote Similarity	NPD7319	Approved
0.6606	Remote Similarity	NPD5697	Approved
0.6606	Remote Similarity	NPD5701	Approved
0.6598	Remote Similarity	NPD4786	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6577	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD7638	Approved
0.6569	Remote Similarity	NPD8171	Discontinued
0.6569	Remote Similarity	NPD6399	Phase 3
0.6542	Remote Similarity	NPD5226	Approved
0.6542	Remote Similarity	NPD5224	Approved
0.6542	Remote Similarity	NPD5225	Approved
0.6542	Remote Similarity	NPD5211	Phase 2
0.6542	Remote Similarity	NPD4633	Approved
0.6538	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5222	Approved
0.6538	Remote Similarity	NPD5221	Approved
0.6529	Remote Similarity	NPD6033	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6509	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD7640	Approved
0.6509	Remote Similarity	NPD8418	Phase 2
0.6486	Remote Similarity	NPD6012	Approved
0.6486	Remote Similarity	NPD6014	Approved
0.6486	Remote Similarity	NPD6013	Approved
0.6481	Remote Similarity	NPD5175	Approved
0.6481	Remote Similarity	NPD5174	Approved
0.6476	Remote Similarity	NPD5173	Approved
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6882	Approved
0.646	Remote Similarity	NPD8297	Approved
0.6449	Remote Similarity	NPD5223	Approved
0.6441	Remote Similarity	NPD6921	Approved
0.6422	Remote Similarity	NPD5141	Approved
0.6408	Remote Similarity	NPD4202	Approved
0.6404	Remote Similarity	NPD4632	Approved
0.6396	Remote Similarity	NPD6011	Approved
0.6392	Remote Similarity	NPD3667	Approved
0.6389	Remote Similarity	NPD7632	Discontinued
0.6379	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7115	Discovery
0.6372	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD6920	Discontinued
0.6354	Remote Similarity	NPD7525	Registered
0.633	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD6084	Phase 2
0.6321	Remote Similarity	NPD6083	Phase 2
0.6316	Remote Similarity	NPD4802	Phase 2
0.6316	Remote Similarity	NPD4238	Approved
0.6286	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4753	Phase 2
0.6261	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.6198	Remote Similarity	NPD8328	Phase 3
0.6198	Remote Similarity	NPD7604	Phase 2
0.6195	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7748	Approved
0.6168	Remote Similarity	NPD7902	Approved
0.6167	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5983	Phase 2
0.6161	Remote Similarity	NPD6412	Phase 2
0.6154	Remote Similarity	NPD6940	Discontinued
0.6154	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5251	Approved
0.614	Remote Similarity	NPD5247	Approved
0.614	Remote Similarity	NPD5248	Approved
0.614	Remote Similarity	NPD5249	Phase 3
0.614	Remote Similarity	NPD5250	Approved
0.6134	Remote Similarity	NPD7100	Approved
0.6134	Remote Similarity	NPD7101	Approved
0.6132	Remote Similarity	NPD4629	Approved
0.6132	Remote Similarity	NPD5210	Approved
0.6132	Remote Similarity	NPD7991	Discontinued
0.6126	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5696	Approved
0.61	Remote Similarity	NPD3666	Approved
0.61	Remote Similarity	NPD3665	Phase 1
0.61	Remote Similarity	NPD3133	Approved
0.6098	Remote Similarity	NPD6336	Discontinued
0.6087	Remote Similarity	NPD5216	Approved
0.6087	Remote Similarity	NPD5217	Approved
0.6087	Remote Similarity	NPD5215	Approved
0.605	Remote Similarity	NPD6335	Approved
0.6044	Remote Similarity	NPD229	Approved
0.6038	Remote Similarity	NPD5282	Discontinued
0.6033	Remote Similarity	NPD6909	Approved
0.6033	Remote Similarity	NPD6908	Approved
0.6017	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD5135	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD5169	Approved
0.6	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6411	Approved
0.5981	Remote Similarity	NPD5695	Phase 3
0.5966	Remote Similarity	NPD6317	Approved
0.5965	Remote Similarity	NPD5168	Approved
0.5965	Remote Similarity	NPD6415	Discontinued
0.596	Remote Similarity	NPD1780	Approved
0.596	Remote Similarity	NPD1779	Approved
0.5955	Remote Similarity	NPD371	Approved
0.5948	Remote Similarity	NPD5127	Approved
0.5941	Remote Similarity	NPD3668	Phase 3
0.5941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6067	Discontinued
0.5917	Remote Similarity	NPD6314	Approved
0.5917	Remote Similarity	NPD7328	Approved
0.5917	Remote Similarity	NPD6313	Approved
0.5917	Remote Similarity	NPD7327	Approved
0.5905	Remote Similarity	NPD6700	Approved
0.5905	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4223	Phase 3
0.59	Remote Similarity	NPD4221	Approved
0.5897	Remote Similarity	NPD6053	Discontinued
0.5888	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6001	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