NPASS Compound

Structure

NPC471887 OpenBabel07101719152D 36 40 0 0 1 0 0 0 0 0999 V2000 6.1964 6.0712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5491 6.6064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2693 3.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9330 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0670 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6244 2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6244 -0.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5709 6.3985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0670 1.6160 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 -1.2990 0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5699 1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1651 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9821 0.4410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1651 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9092 4.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6220 3.7532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2182 5.8632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2912 3.0101 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9310 4.7043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9821 2.0590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1651 0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4330 0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2990 -0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4330 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4330 -1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0311 1.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0311 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2990 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4330 -0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1651 -1.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2619 5.4474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0670 1.6160 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 20 1 0 0 0 0 2 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 2 0 0 0 0 13 24 1 0 0 0 0 14 30 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 18 20 2 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 21 3 1 1 0 0 0 21 23 1 0 0 0 0 22 18 1 1 0 0 0 22 34 1 0 0 0 0 23 29 1 1 0 0 0 24 30 1 6 0 0 0 24 31 1 0 0 0 0 25 31 1 1 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 33 1 1 0 0 0 27 31 1 1 0 0 0 27 35 1 0 0 0 0 27 36 1 0 0 0 0 28 32 1 0 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 31 17 1 6 0 0 0 32 15 1 1 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.39
Volume:	549.134
LogP:	6.711
LogD:	5.055
LogS:	-6.173
# Rotatable Bonds:	6
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	6.781
Fsp3:	0.875
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:	-4.867
MDCK Permeability:	1.591590444149915e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	92.38570404052734%
Volume Distribution (VD):	1.586
Pgp-substrate:	4.43967342376709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.838

ADMET: Excretion

Clearance (CL):	8.3
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.522
Human Hepatotoxicity (H-HT):	0.61
Drug-inuced Liver Injury (DILI):	0.203
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.804
Maximum Recommended Daily Dose:	0.756
Skin Sensitization:	0.677
Carcinogencity:	0.048
Eye Corrosion:	0.005
Eye Irritation:	0.026
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC471887

Natural Product ID:	NPC471887
*Common Name:**	CRZHMFVUXYIFSA-ZUWLVCODSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CRZHMFVUXYIFSA-ZUWLVCODSA-N
Standard InCHI:	InChI=1S/C32H52O4/c1-20(2)18-22(34-8)19-21(3)23-12-14-30(7)24-13-15-32-25(10-11-26(33)28(32,4)5)31(24,27(35-9)36-32)17-16-29(23,30)6/h13,15,18,21-27,33H,10-12,14,16-17,19H2,1-9H3/t21-,22+,23-,24+,25+,26+,27-,29-,30+,31+,32-/m1/s1
SMILES:	CO[C@H](C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2C=C[C@]2([C@H]3CC[C@@H](C2(C)C)O)O[C@H]1OC)C)C)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3264661
PubChem CID:	90677197
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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	=	40.0	%	PMID[492807]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	32.0	%	PMID[492807]

☑ 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 NPC471887 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	226
0.1-0.2	1543
0.2-0.3	5086
0.3-0.4	12252
0.4-0.5	10240
0.5-0.6	6433
0.6-0.7	5095
0.7-0.8	1643
0.8-0.85	134
0.85-0.9	15
0.9-0.95	21
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471885
1.0	High Similarity	NPC471888
1.0	High Similarity	NPC471886
0.9895	High Similarity	NPC37207
0.9688	High Similarity	NPC300399
0.9688	High Similarity	NPC471482
0.9588	High Similarity	NPC471450
0.9485	High Similarity	NPC471889
0.9406	High Similarity	NPC103627
0.9406	High Similarity	NPC191439
0.9406	High Similarity	NPC170974
0.9314	High Similarity	NPC65034
0.9314	High Similarity	NPC208189
0.9307	High Similarity	NPC473318
0.9307	High Similarity	NPC473328
0.9307	High Similarity	NPC28844
0.9223	High Similarity	NPC231797
0.9216	High Similarity	NPC65155
0.898	High Similarity	NPC5358
0.898	High Similarity	NPC216260
0.8958	High Similarity	NPC144202
0.8932	High Similarity	NPC250089
0.8932	High Similarity	NPC14630
0.8932	High Similarity	NPC157530
0.8922	High Similarity	NPC33053
0.8889	High Similarity	NPC324598
0.8857	High Similarity	NPC473567
0.8857	High Similarity	NPC216595
0.8854	High Similarity	NPC27531
0.88	High Similarity	NPC21568
0.88	High Similarity	NPC285231
0.88	High Similarity	NPC176406
0.8725	High Similarity	NPC85593
0.8725	High Similarity	NPC93352
0.8725	High Similarity	NPC31430
0.8673	High Similarity	NPC135224
0.8673	High Similarity	NPC477970
0.8673	High Similarity	NPC477969
0.8673	High Similarity	NPC100892
0.8627	High Similarity	NPC213190
0.8614	High Similarity	NPC474022
0.8586	High Similarity	NPC12103
0.8586	High Similarity	NPC227583
0.8586	High Similarity	NPC98457
0.8585	High Similarity	NPC13190
0.8571	High Similarity	NPC128133
0.8571	High Similarity	NPC472901
0.8571	High Similarity	NPC189513
0.8558	High Similarity	NPC226642
0.8544	High Similarity	NPC75608
0.8542	High Similarity	NPC470819
0.8505	High Similarity	NPC475354
0.8505	High Similarity	NPC112274
0.85	High Similarity	NPC177818
0.8485	Intermediate Similarity	NPC8774
0.8476	Intermediate Similarity	NPC38376
0.8476	Intermediate Similarity	NPC235824
0.8476	Intermediate Similarity	NPC80210
0.8462	Intermediate Similarity	NPC26798
0.8462	Intermediate Similarity	NPC472900
0.8462	Intermediate Similarity	NPC472898
0.8462	Intermediate Similarity	NPC472899
0.8454	Intermediate Similarity	NPC470817
0.8454	Intermediate Similarity	NPC295668
0.8447	Intermediate Similarity	NPC120009
0.8431	Intermediate Similarity	NPC88000
0.8431	Intermediate Similarity	NPC47566
0.8431	Intermediate Similarity	NPC4831
0.8431	Intermediate Similarity	NPC470434
0.8431	Intermediate Similarity	NPC160734
0.8431	Intermediate Similarity	NPC129372
0.8431	Intermediate Similarity	NPC309425
0.8431	Intermediate Similarity	NPC472023
0.8426	Intermediate Similarity	NPC51154
0.8416	Intermediate Similarity	NPC158088
0.8416	Intermediate Similarity	NPC234287
0.8416	Intermediate Similarity	NPC280825
0.8411	Intermediate Similarity	NPC472987
0.8411	Intermediate Similarity	NPC473021
0.8407	Intermediate Similarity	NPC41129
0.84	Intermediate Similarity	NPC288970
0.8396	Intermediate Similarity	NPC285253
0.8396	Intermediate Similarity	NPC221110
0.8396	Intermediate Similarity	NPC180459
0.8396	Intermediate Similarity	NPC195116
0.8384	Intermediate Similarity	NPC65402
0.8384	Intermediate Similarity	NPC127718
0.8381	Intermediate Similarity	NPC231340
0.8365	Intermediate Similarity	NPC470885
0.8365	Intermediate Similarity	NPC475365
0.8365	Intermediate Similarity	NPC187400
0.8365	Intermediate Similarity	NPC221562
0.8364	Intermediate Similarity	NPC20979
0.8364	Intermediate Similarity	NPC476690
0.8364	Intermediate Similarity	NPC100048
0.835	Intermediate Similarity	NPC471363
0.835	Intermediate Similarity	NPC136816
0.835	Intermediate Similarity	NPC238397
0.8349	Intermediate Similarity	NPC11548
0.8333	Intermediate Similarity	NPC477972
0.8333	Intermediate Similarity	NPC20113
0.8333	Intermediate Similarity	NPC228251
0.8333	Intermediate Similarity	NPC477971
0.8333	Intermediate Similarity	NPC477968
0.8333	Intermediate Similarity	NPC469942
0.8333	Intermediate Similarity	NPC473200
0.8333	Intermediate Similarity	NPC161527
0.8333	Intermediate Similarity	NPC7341
0.8333	Intermediate Similarity	NPC219285
0.8318	Intermediate Similarity	NPC101450
0.8317	Intermediate Similarity	NPC473890
0.8317	Intermediate Similarity	NPC243728
0.8302	Intermediate Similarity	NPC472897
0.8302	Intermediate Similarity	NPC472896
0.8302	Intermediate Similarity	NPC476540
0.8302	Intermediate Similarity	NPC476541
0.8302	Intermediate Similarity	NPC476539
0.8302	Intermediate Similarity	NPC476538
0.8302	Intermediate Similarity	NPC220427
0.8288	Intermediate Similarity	NPC10366
0.8286	Intermediate Similarity	NPC476592
0.8286	Intermediate Similarity	NPC474015
0.8283	Intermediate Similarity	NPC474792
0.8283	Intermediate Similarity	NPC67398
0.8283	Intermediate Similarity	NPC91654
0.8273	Intermediate Similarity	NPC477029
0.8273	Intermediate Similarity	NPC477030
0.8269	Intermediate Similarity	NPC31907
0.8269	Intermediate Similarity	NPC7644
0.8269	Intermediate Similarity	NPC472252
0.8269	Intermediate Similarity	NPC473020
0.8269	Intermediate Similarity	NPC120123
0.8269	Intermediate Similarity	NPC131479
0.8269	Intermediate Similarity	NPC286969
0.8269	Intermediate Similarity	NPC127933
0.8269	Intermediate Similarity	NPC189852
0.8269	Intermediate Similarity	NPC16520
0.8269	Intermediate Similarity	NPC473124
0.8269	Intermediate Similarity	NPC7613
0.8269	Intermediate Similarity	NPC475701
0.8269	Intermediate Similarity	NPC157659
0.8269	Intermediate Similarity	NPC134270
0.8269	Intermediate Similarity	NPC245280
0.8269	Intermediate Similarity	NPC473523
0.8269	Intermediate Similarity	NPC155010
0.8269	Intermediate Similarity	NPC8039
0.8269	Intermediate Similarity	NPC475889
0.8269	Intermediate Similarity	NPC473198
0.8269	Intermediate Similarity	NPC473123
0.8269	Intermediate Similarity	NPC114874
0.8269	Intermediate Similarity	NPC211879
0.8257	Intermediate Similarity	NPC469348
0.8257	Intermediate Similarity	NPC469347
0.8252	Intermediate Similarity	NPC267510
0.8241	Intermediate Similarity	NPC197231
0.8241	Intermediate Similarity	NPC110494
0.8241	Intermediate Similarity	NPC157474
0.8229	Intermediate Similarity	NPC299068
0.8224	Intermediate Similarity	NPC70204
0.8224	Intermediate Similarity	NPC477026
0.8224	Intermediate Similarity	NPC206618
0.8224	Intermediate Similarity	NPC476835
0.8224	Intermediate Similarity	NPC306131
0.8224	Intermediate Similarity	NPC477027
0.8224	Intermediate Similarity	NPC475670
0.8224	Intermediate Similarity	NPC475030
0.8218	Intermediate Similarity	NPC207617
0.8218	Intermediate Similarity	NPC90583
0.8214	Intermediate Similarity	NPC477071
0.8211	Intermediate Similarity	NPC470077
0.8208	Intermediate Similarity	NPC190395
0.8208	Intermediate Similarity	NPC109376
0.8208	Intermediate Similarity	NPC476594
0.8208	Intermediate Similarity	NPC475074
0.8208	Intermediate Similarity	NPC475781
0.82	Intermediate Similarity	NPC305160
0.8198	Intermediate Similarity	NPC196429
0.8198	Intermediate Similarity	NPC471355
0.8198	Intermediate Similarity	NPC244402
0.8198	Intermediate Similarity	NPC99728
0.8198	Intermediate Similarity	NPC203862
0.8198	Intermediate Similarity	NPC471351
0.8198	Intermediate Similarity	NPC50305
0.8198	Intermediate Similarity	NPC34390
0.8198	Intermediate Similarity	NPC77319
0.8198	Intermediate Similarity	NPC93883
0.8198	Intermediate Similarity	NPC84987
0.8198	Intermediate Similarity	NPC27507
0.8198	Intermediate Similarity	NPC471354
0.8198	Intermediate Similarity	NPC142066
0.8198	Intermediate Similarity	NPC87250
0.8198	Intermediate Similarity	NPC157376
0.8198	Intermediate Similarity	NPC471353
0.8198	Intermediate Similarity	NPC158344
0.8198	Intermediate Similarity	NPC473852
0.8198	Intermediate Similarity	NPC474418
0.8198	Intermediate Similarity	NPC309034
0.8198	Intermediate Similarity	NPC243196
0.819	Intermediate Similarity	NPC201880
0.819	Intermediate Similarity	NPC165033

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 NPC471887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1699
0.2-0.3	4157
0.3-0.4	2132
0.4-0.5	516
0.5-0.6	228
0.6-0.7	183
0.7-0.8	39
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD7327	Approved
0.8125	Intermediate Similarity	NPD7328	Approved
0.807	Intermediate Similarity	NPD8380	Approved
0.807	Intermediate Similarity	NPD8296	Approved
0.807	Intermediate Similarity	NPD8378	Approved
0.807	Intermediate Similarity	NPD8379	Approved
0.807	Intermediate Similarity	NPD8335	Approved
0.8053	Intermediate Similarity	NPD7516	Approved
0.7982	Intermediate Similarity	NPD8377	Approved
0.7982	Intermediate Similarity	NPD8294	Approved
0.7913	Intermediate Similarity	NPD8033	Approved
0.7759	Intermediate Similarity	NPD7503	Approved
0.7604	Intermediate Similarity	NPD7525	Registered
0.7547	Intermediate Similarity	NPD7638	Approved
0.7542	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD7507	Approved
0.7477	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7319	Approved
0.7377	Intermediate Similarity	NPD7736	Approved
0.7374	Intermediate Similarity	NPD6695	Phase 3
0.7373	Intermediate Similarity	NPD6054	Approved
0.7295	Intermediate Similarity	NPD8293	Discontinued
0.7255	Intermediate Similarity	NPD7750	Discontinued
0.7232	Intermediate Similarity	NPD6412	Phase 2
0.7227	Intermediate Similarity	NPD6059	Approved
0.7168	Intermediate Similarity	NPD6686	Approved
0.7167	Intermediate Similarity	NPD6016	Approved
0.7167	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD8133	Approved
0.7131	Intermediate Similarity	NPD7492	Approved
0.7107	Intermediate Similarity	NPD5988	Approved
0.7087	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7524	Approved
0.7083	Intermediate Similarity	NPD6942	Approved
0.7083	Intermediate Similarity	NPD7339	Approved
0.7073	Intermediate Similarity	NPD6616	Approved
0.7071	Intermediate Similarity	NPD7514	Phase 3
0.7071	Intermediate Similarity	NPD6930	Phase 2
0.7071	Intermediate Similarity	NPD6931	Approved
0.7069	Intermediate Similarity	NPD6882	Approved
0.7016	Intermediate Similarity	NPD7078	Approved
0.697	Remote Similarity	NPD6929	Approved
0.697	Remote Similarity	NPD7645	Phase 2
0.6952	Remote Similarity	NPD6051	Approved
0.6939	Remote Similarity	NPD6932	Approved
0.6916	Remote Similarity	NPD8171	Discontinued
0.6911	Remote Similarity	NPD6067	Discontinued
0.69	Remote Similarity	NPD6928	Phase 2
0.69	Remote Similarity	NPD7332	Phase 2
0.6875	Remote Similarity	NPD7632	Discontinued
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.687	Remote Similarity	NPD7320	Approved
0.6869	Remote Similarity	NPD7145	Approved
0.6842	Remote Similarity	NPD6402	Approved
0.6842	Remote Similarity	NPD7128	Approved
0.6842	Remote Similarity	NPD5739	Approved
0.6842	Remote Similarity	NPD6675	Approved
0.6838	Remote Similarity	NPD8130	Phase 1
0.6837	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6009	Approved
0.6833	Remote Similarity	NPD7115	Discovery
0.6832	Remote Similarity	NPD6902	Approved
0.6822	Remote Similarity	NPD7637	Suspended
0.6822	Remote Similarity	NPD7087	Discontinued
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5697	Approved
0.678	Remote Similarity	NPD8297	Approved
0.6768	Remote Similarity	NPD5776	Phase 2
0.6768	Remote Similarity	NPD6925	Approved
0.6759	Remote Similarity	NPD6399	Phase 3
0.6752	Remote Similarity	NPD7290	Approved
0.6752	Remote Similarity	NPD6883	Approved
0.6752	Remote Similarity	NPD7102	Approved
0.6748	Remote Similarity	NPD8515	Approved
0.6748	Remote Similarity	NPD8513	Phase 3
0.6748	Remote Similarity	NPD8517	Approved
0.6748	Remote Similarity	NPD8516	Approved
0.6731	Remote Similarity	NPD6893	Approved
0.6726	Remote Similarity	NPD5211	Phase 2
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD5285	Approved
0.6696	Remote Similarity	NPD5286	Approved
0.6696	Remote Similarity	NPD4696	Approved
0.6695	Remote Similarity	NPD6847	Approved
0.6695	Remote Similarity	NPD6649	Approved
0.6695	Remote Similarity	NPD6650	Approved
0.6695	Remote Similarity	NPD6617	Approved
0.6695	Remote Similarity	NPD6869	Approved
0.6693	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6638	Remote Similarity	NPD5701	Approved
0.6637	Remote Similarity	NPD5344	Discontinued
0.6637	Remote Similarity	NPD4159	Approved
0.6636	Remote Similarity	NPD5328	Approved
0.6635	Remote Similarity	NPD4786	Approved
0.6634	Remote Similarity	NPD6683	Phase 2
0.6633	Remote Similarity	NPD6924	Approved
0.6633	Remote Similarity	NPD4784	Approved
0.6633	Remote Similarity	NPD4785	Approved
0.6633	Remote Similarity	NPD6926	Approved
0.6615	Remote Similarity	NPD8449	Approved
0.661	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5141	Approved
0.6607	Remote Similarity	NPD4225	Approved
0.6606	Remote Similarity	NPD4202	Approved
0.6598	Remote Similarity	NPD4243	Approved
0.6583	Remote Similarity	NPD4632	Approved
0.6581	Remote Similarity	NPD6011	Approved
0.6579	Remote Similarity	NPD4633	Approved
0.6579	Remote Similarity	NPD5225	Approved
0.6579	Remote Similarity	NPD5224	Approved
0.6579	Remote Similarity	NPD5226	Approved
0.6565	Remote Similarity	NPD8450	Suspended
0.6549	Remote Similarity	NPD4700	Approved
0.6532	Remote Similarity	NPD7741	Discontinued
0.6532	Remote Similarity	NPD6319	Approved
0.6522	Remote Similarity	NPD5175	Approved
0.6522	Remote Similarity	NPD5174	Approved
0.6518	Remote Similarity	NPD6083	Phase 2
0.6518	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD8035	Phase 2
0.6514	Remote Similarity	NPD8034	Phase 2
0.6509	Remote Similarity	NPD3618	Phase 1
0.6508	Remote Similarity	NPD8328	Phase 3
0.6505	Remote Similarity	NPD6898	Phase 1
0.65	Remote Similarity	NPD6933	Approved
0.6491	Remote Similarity	NPD5223	Approved
0.6476	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4634	Approved
0.6442	Remote Similarity	NPD3667	Approved
0.6441	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7152	Approved
0.6429	Remote Similarity	NPD7151	Approved
0.6429	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5221	Approved
0.6429	Remote Similarity	NPD7150	Approved
0.6423	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4748	Discontinued
0.6408	Remote Similarity	NPD7509	Discontinued
0.6404	Remote Similarity	NPD6648	Approved
0.64	Remote Similarity	NPD8264	Approved
0.6396	Remote Similarity	NPD7748	Approved
0.6378	Remote Similarity	NPD7604	Phase 2
0.6373	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7902	Approved
0.6372	Remote Similarity	NPD5173	Approved
0.6357	Remote Similarity	NPD7625	Phase 1
0.6356	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5983	Phase 2
0.6339	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD5956	Approved
0.633	Remote Similarity	NPD4753	Phase 2
0.6327	Remote Similarity	NPD7144	Approved
0.6327	Remote Similarity	NPD7143	Approved
0.6325	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD7101	Approved
0.6311	Remote Similarity	NPD4195	Approved
0.6303	Remote Similarity	NPD4730	Approved
0.6303	Remote Similarity	NPD4729	Approved
0.6283	Remote Similarity	NPD4697	Phase 3
0.6281	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6336	Discontinued
0.6273	Remote Similarity	NPD3168	Discontinued
0.6271	Remote Similarity	NPD4767	Approved
0.6271	Remote Similarity	NPD4768	Approved
0.6262	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6335	Approved
0.6239	Remote Similarity	NPD4754	Approved
0.6238	Remote Similarity	NPD4190	Phase 3
0.6238	Remote Similarity	NPD5275	Approved
0.6231	Remote Similarity	NPD8074	Phase 3
0.6224	Remote Similarity	NPD6922	Approved
0.6224	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6923	Approved
0.622	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7515	Phase 2
0.621	Remote Similarity	NPD6274	Approved
0.6198	Remote Similarity	NPD5249	Phase 3
0.6198	Remote Similarity	NPD5247	Approved
0.6198	Remote Similarity	NPD5248	Approved
0.6198	Remote Similarity	NPD5250	Approved
0.6198	Remote Similarity	NPD5251	Approved
0.6195	Remote Similarity	NPD5695	Phase 3
0.6195	Remote Similarity	NPD7991	Discontinued
0.6195	Remote Similarity	NPD5210	Approved
0.6195	Remote Similarity	NPD4629	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