NPASS Compound

Structure

NPC474484 OpenBabel07101719142D 33 37 0 0 1 0 0 0 0 0999 V2000 4.7090 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5034 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0165 0.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0281 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1051 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1337 -2.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7566 0.7401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -0.1860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4060 2.3897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1653 -2.4518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 19 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 1 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 33 2 0 0 0 0 25 30 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	4.552
LogD:	4.565
LogS:	-4.786
# Rotatable Bonds:	3
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	4.887
Fsp3:	0.9
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:	-5.163
MDCK Permeability:	1.0320153705833945e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.773
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.183
Plasma Protein Binding (PPB):	87.8738021850586%
Volume Distribution (VD):	0.881
Pgp-substrate:	2.719571352005005%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.357
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.179
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.656
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	4.98
Half-life (T1/2):	0.52

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.537
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.249
Carcinogencity:	0.06
Eye Corrosion:	0.063
Eye Irritation:	0.51
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC474484

Natural Product ID:	NPC474484
*Common Name:**	28,30-Dihydroxy-3-Oxolup-20(29)-Ene
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aS,13bS)-3a-(hydroxymethyl)-1-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a-pentamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:
Standard InCHIKey:	MYNVTABAVQTEMV-CAUXFXQKSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(17-31)20-9-14-30(18-32)16-15-28(5)21(25(20)30)7-8-23-27(4)12-11-24(33)26(2,3)22(27)10-13-29(23,28)6/h20-23,25,31-32H,1,7-18H2,2-6H3/t20-,21-,22-,23+,25+,27-,28+,29+,30+/m0/s1
SMILES:	CC1(C2CCC3(C(C2(CCC1=O)C)CCC4C3(CCC5(C4C(CC5)C(=C)CO)CO)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469831
PubChem CID:	44559220
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1333	Maytenus chiapensis	Species	Celastraceae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4.0	ug.mL-1	PMID[524042]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	7.1	ug.mL-1	PMID[524042]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	10.0	ug.mL-1	PMID[524042]

☑ 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 NPC474484 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	165
0.1-0.2	1579
0.2-0.3	7663
0.3-0.4	15734
0.4-0.5	6425
0.5-0.6	5412
0.6-0.7	4126
0.7-0.8	1433
0.8-0.85	109
0.85-0.9	34
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103754
0.9733	High Similarity	NPC201459
0.9494	High Similarity	NPC292553
0.9375	High Similarity	NPC472738
0.9359	High Similarity	NPC477858
0.9359	High Similarity	NPC145143
0.9259	High Similarity	NPC4643
0.9241	High Similarity	NPC175410
0.9241	High Similarity	NPC472743
0.9241	High Similarity	NPC475726
0.9125	High Similarity	NPC474233
0.9125	High Similarity	NPC475745
0.9125	High Similarity	NPC474482
0.9012	High Similarity	NPC201655
0.9	High Similarity	NPC472740
0.8974	High Similarity	NPC192744
0.8961	High Similarity	NPC106078
0.8916	High Similarity	NPC16377
0.8902	High Similarity	NPC70661
0.8889	High Similarity	NPC264665
0.8889	High Similarity	NPC74595
0.8875	High Similarity	NPC46881
0.8795	High Similarity	NPC57469
0.878	High Similarity	NPC471224
0.878	High Similarity	NPC294438
0.878	High Similarity	NPC264317
0.8765	High Similarity	NPC472498
0.8718	High Similarity	NPC68828
0.869	High Similarity	NPC472739
0.869	High Similarity	NPC474719
0.8675	High Similarity	NPC269396
0.8675	High Similarity	NPC98236
0.8675	High Similarity	NPC2783
0.8675	High Similarity	NPC12774
0.8675	High Similarity	NPC469994
0.8659	High Similarity	NPC263974
0.8642	High Similarity	NPC170985
0.8625	High Similarity	NPC164999
0.8608	High Similarity	NPC63020
0.8571	High Similarity	NPC93778
0.8571	High Similarity	NPC33768
0.8571	High Similarity	NPC264005
0.8571	High Similarity	NPC269360
0.8554	High Similarity	NPC274724
0.8554	High Similarity	NPC76518
0.8554	High Similarity	NPC474083
0.8537	High Similarity	NPC245866
0.8519	High Similarity	NPC164210
0.8519	High Similarity	NPC3915
0.85	High Similarity	NPC215843
0.8481	Intermediate Similarity	NPC66105
0.8481	Intermediate Similarity	NPC212241
0.8481	Intermediate Similarity	NPC248830
0.8481	Intermediate Similarity	NPC119355
0.8471	Intermediate Similarity	NPC471900
0.8434	Intermediate Similarity	NPC59453
0.8434	Intermediate Similarity	NPC221758
0.8434	Intermediate Similarity	NPC214043
0.8434	Intermediate Similarity	NPC473157
0.8434	Intermediate Similarity	NPC85774
0.8434	Intermediate Similarity	NPC82902
0.8415	Intermediate Similarity	NPC310989
0.8415	Intermediate Similarity	NPC110780
0.8372	Intermediate Similarity	NPC2983
0.8372	Intermediate Similarity	NPC213832
0.8372	Intermediate Similarity	NPC57954
0.8372	Intermediate Similarity	NPC220498
0.8372	Intermediate Similarity	NPC473999
0.8372	Intermediate Similarity	NPC309603
0.8354	Intermediate Similarity	NPC246445
0.8353	Intermediate Similarity	NPC472495
0.8353	Intermediate Similarity	NPC317590
0.8353	Intermediate Similarity	NPC472497
0.8333	Intermediate Similarity	NPC474218
0.8333	Intermediate Similarity	NPC469948
0.8313	Intermediate Similarity	NPC471036
0.8313	Intermediate Similarity	NPC291320
0.8313	Intermediate Similarity	NPC118800
0.8295	Intermediate Similarity	NPC244356
0.8295	Intermediate Similarity	NPC224060
0.8293	Intermediate Similarity	NPC328264
0.8276	Intermediate Similarity	NPC169933
0.8276	Intermediate Similarity	NPC48010
0.8256	Intermediate Similarity	NPC4309
0.8256	Intermediate Similarity	NPC193360
0.825	Intermediate Similarity	NPC149249
0.825	Intermediate Similarity	NPC471035
0.825	Intermediate Similarity	NPC212661
0.8235	Intermediate Similarity	NPC475007
0.8235	Intermediate Similarity	NPC51014
0.8235	Intermediate Similarity	NPC145879
0.8235	Intermediate Similarity	NPC474733
0.8235	Intermediate Similarity	NPC474732
0.8235	Intermediate Similarity	NPC80590
0.8235	Intermediate Similarity	NPC474778
0.8235	Intermediate Similarity	NPC187545
0.8235	Intermediate Similarity	NPC31564
0.8228	Intermediate Similarity	NPC212879
0.8228	Intermediate Similarity	NPC104387
0.8228	Intermediate Similarity	NPC174964
0.8228	Intermediate Similarity	NPC195155
0.8228	Intermediate Similarity	NPC231256
0.8228	Intermediate Similarity	NPC178383
0.8228	Intermediate Similarity	NPC240235
0.8228	Intermediate Similarity	NPC97534
0.8228	Intermediate Similarity	NPC185536
0.8214	Intermediate Similarity	NPC227132
0.8214	Intermediate Similarity	NPC180834
0.8214	Intermediate Similarity	NPC165064
0.8214	Intermediate Similarity	NPC473246
0.8214	Intermediate Similarity	NPC237712
0.8214	Intermediate Similarity	NPC476038
0.8214	Intermediate Similarity	NPC194937
0.8214	Intermediate Similarity	NPC146683
0.8205	Intermediate Similarity	NPC36310
0.8205	Intermediate Similarity	NPC472506
0.8205	Intermediate Similarity	NPC330659
0.8205	Intermediate Similarity	NPC244708
0.8205	Intermediate Similarity	NPC161187
0.8193	Intermediate Similarity	NPC151519
0.8182	Intermediate Similarity	NPC272746
0.8182	Intermediate Similarity	NPC473998
0.8182	Intermediate Similarity	NPC475806
0.8182	Intermediate Similarity	NPC475416
0.8171	Intermediate Similarity	NPC472478
0.8161	Intermediate Similarity	NPC122116
0.8161	Intermediate Similarity	NPC281524
0.8161	Intermediate Similarity	NPC271974
0.8161	Intermediate Similarity	NPC229871
0.8161	Intermediate Similarity	NPC247312
0.8161	Intermediate Similarity	NPC469319
0.8158	Intermediate Similarity	NPC473225
0.8148	Intermediate Similarity	NPC82635
0.814	Intermediate Similarity	NPC96496
0.814	Intermediate Similarity	NPC134197
0.814	Intermediate Similarity	NPC475740
0.814	Intermediate Similarity	NPC90652
0.814	Intermediate Similarity	NPC58063
0.8133	Intermediate Similarity	NPC43300
0.8125	Intermediate Similarity	NPC86305
0.8125	Intermediate Similarity	NPC5767
0.8125	Intermediate Similarity	NPC278091
0.8125	Intermediate Similarity	NPC475742
0.8125	Intermediate Similarity	NPC20466
0.8125	Intermediate Similarity	NPC14112
0.8125	Intermediate Similarity	NPC93662
0.8125	Intermediate Similarity	NPC78067
0.8118	Intermediate Similarity	NPC190704
0.8118	Intermediate Similarity	NPC102292
0.8118	Intermediate Similarity	NPC283733
0.8118	Intermediate Similarity	NPC133954
0.8118	Intermediate Similarity	NPC471034
0.8111	Intermediate Similarity	NPC476174
0.8101	Intermediate Similarity	NPC25511
0.8101	Intermediate Similarity	NPC159497
0.8101	Intermediate Similarity	NPC62657
0.8101	Intermediate Similarity	NPC476736
0.8101	Intermediate Similarity	NPC192638
0.8095	Intermediate Similarity	NPC215893
0.8095	Intermediate Similarity	NPC471037
0.809	Intermediate Similarity	NPC291373
0.809	Intermediate Similarity	NPC474736
0.809	Intermediate Similarity	NPC471902
0.809	Intermediate Similarity	NPC473690
0.809	Intermediate Similarity	NPC287118
0.8077	Intermediate Similarity	NPC320549
0.8077	Intermediate Similarity	NPC58057
0.8077	Intermediate Similarity	NPC164045
0.8077	Intermediate Similarity	NPC151018
0.8077	Intermediate Similarity	NPC156277
0.8072	Intermediate Similarity	NPC147066
0.8068	Intermediate Similarity	NPC100313
0.8068	Intermediate Similarity	NPC85173
0.8068	Intermediate Similarity	NPC320026
0.8068	Intermediate Similarity	NPC126993
0.8068	Intermediate Similarity	NPC69622
0.8068	Intermediate Similarity	NPC46758
0.8052	Intermediate Similarity	NPC475952
0.8049	Intermediate Similarity	NPC476812
0.8049	Intermediate Similarity	NPC472490
0.8049	Intermediate Similarity	NPC471475
0.8046	Intermediate Similarity	NPC470417
0.8046	Intermediate Similarity	NPC211162
0.8046	Intermediate Similarity	NPC146937
0.8046	Intermediate Similarity	NPC183374
0.8046	Intermediate Similarity	NPC328313
0.8025	Intermediate Similarity	NPC202540
0.8025	Intermediate Similarity	NPC23884
0.8025	Intermediate Similarity	NPC472746
0.8025	Intermediate Similarity	NPC257191
0.8025	Intermediate Similarity	NPC221420
0.8025	Intermediate Similarity	NPC331618
0.8025	Intermediate Similarity	NPC476811
0.8023	Intermediate Similarity	NPC473168
0.8023	Intermediate Similarity	NPC213412
0.8023	Intermediate Similarity	NPC471737
0.8023	Intermediate Similarity	NPC72133
0.8023	Intermediate Similarity	NPC475862
0.8023	Intermediate Similarity	NPC168231
0.8023	Intermediate Similarity	NPC155011

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 NPC474484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	2012
0.2-0.3	4388
0.3-0.4	1780
0.4-0.5	394
0.5-0.6	163
0.6-0.7	185
0.7-0.8	67
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD7520	Clinical (unspecified phase)
0.8765	High Similarity	NPD4788	Approved
0.8434	Intermediate Similarity	NPD4786	Approved
0.8193	Intermediate Similarity	NPD3667	Approved
0.8182	Intermediate Similarity	NPD4789	Approved
0.8077	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3665	Phase 1
0.8	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3666	Approved
0.8	Intermediate Similarity	NPD3133	Approved
0.7978	Intermediate Similarity	NPD8035	Phase 2
0.7978	Intermediate Similarity	NPD8034	Phase 2
0.7955	Intermediate Similarity	NPD5328	Approved
0.7949	Intermediate Similarity	NPD4244	Approved
0.7949	Intermediate Similarity	NPD4245	Approved
0.7821	Intermediate Similarity	NPD3698	Phase 2
0.7821	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD6079	Approved
0.7765	Intermediate Similarity	NPD4221	Approved
0.7765	Intermediate Similarity	NPD4223	Phase 3
0.7753	Intermediate Similarity	NPD4753	Phase 2
0.7701	Intermediate Similarity	NPD5329	Approved
0.7692	Intermediate Similarity	NPD5360	Phase 3
0.7692	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5279	Phase 3
0.7586	Intermediate Similarity	NPD4197	Approved
0.7582	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD3617	Approved
0.747	Intermediate Similarity	NPD6117	Approved
0.7444	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4224	Phase 2
0.7416	Intermediate Similarity	NPD4689	Approved
0.7416	Intermediate Similarity	NPD4138	Approved
0.7416	Intermediate Similarity	NPD5205	Approved
0.7416	Intermediate Similarity	NPD4690	Approved
0.7416	Intermediate Similarity	NPD4693	Phase 3
0.7416	Intermediate Similarity	NPD4688	Approved
0.7407	Intermediate Similarity	NPD6081	Approved
0.7386	Intermediate Similarity	NPD3668	Phase 3
0.7381	Intermediate Similarity	NPD6116	Phase 1
0.7368	Intermediate Similarity	NPD6084	Phase 2
0.7368	Intermediate Similarity	NPD6083	Phase 2
0.7349	Intermediate Similarity	NPD7339	Approved
0.7349	Intermediate Similarity	NPD3703	Phase 2
0.7349	Intermediate Similarity	NPD6942	Approved
0.734	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD4629	Approved
0.7326	Intermediate Similarity	NPD7525	Registered
0.7294	Intermediate Similarity	NPD6114	Approved
0.7294	Intermediate Similarity	NPD6118	Approved
0.7294	Intermediate Similarity	NPD6115	Approved
0.7294	Intermediate Similarity	NPD6697	Approved
0.7263	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5222	Approved
0.7263	Intermediate Similarity	NPD4697	Phase 3
0.7263	Intermediate Similarity	NPD5221	Approved
0.7253	Intermediate Similarity	NPD6672	Approved
0.7253	Intermediate Similarity	NPD5737	Approved
0.7245	Intermediate Similarity	NPD5211	Phase 2
0.7241	Intermediate Similarity	NPD4692	Approved
0.7241	Intermediate Similarity	NPD4139	Approved
0.7234	Intermediate Similarity	NPD7748	Approved
0.7222	Intermediate Similarity	NPD5690	Phase 2
0.7222	Intermediate Similarity	NPD5330	Approved
0.7222	Intermediate Similarity	NPD4623	Approved
0.7222	Intermediate Similarity	NPD6684	Approved
0.7222	Intermediate Similarity	NPD7334	Approved
0.7222	Intermediate Similarity	NPD4694	Approved
0.7222	Intermediate Similarity	NPD7521	Approved
0.7222	Intermediate Similarity	NPD4519	Discontinued
0.7222	Intermediate Similarity	NPD5280	Approved
0.7222	Intermediate Similarity	NPD7146	Approved
0.7222	Intermediate Similarity	NPD6409	Approved
0.7195	Intermediate Similarity	NPD4758	Discontinued
0.7188	Intermediate Similarity	NPD4755	Approved
0.7188	Intermediate Similarity	NPD5173	Approved
0.71	Intermediate Similarity	NPD5141	Approved
0.7093	Intermediate Similarity	NPD3671	Phase 1
0.7093	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4747	Approved
0.7065	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7639	Approved
0.7041	Intermediate Similarity	NPD4700	Approved
0.7041	Intermediate Similarity	NPD5286	Approved
0.7041	Intermediate Similarity	NPD4696	Approved
0.7041	Intermediate Similarity	NPD5285	Approved
0.7041	Intermediate Similarity	NPD7640	Approved
0.7033	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6098	Approved
0.7024	Intermediate Similarity	NPD6924	Approved
0.7024	Intermediate Similarity	NPD6926	Approved
0.7011	Intermediate Similarity	NPD6929	Approved
0.7011	Intermediate Similarity	NPD7645	Phase 2
0.7011	Intermediate Similarity	NPD4195	Approved
0.701	Intermediate Similarity	NPD7902	Approved
0.6988	Remote Similarity	NPD4243	Approved
0.6988	Remote Similarity	NPD5777	Approved
0.6979	Remote Similarity	NPD5695	Phase 3
0.697	Remote Similarity	NPD5223	Approved
0.6951	Remote Similarity	NPD4137	Phase 3
0.6941	Remote Similarity	NPD3702	Approved
0.6939	Remote Similarity	NPD5696	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6932	Remote Similarity	NPD6931	Approved
0.6932	Remote Similarity	NPD4695	Discontinued
0.6932	Remote Similarity	NPD6930	Phase 2
0.69	Remote Similarity	NPD5225	Approved
0.69	Remote Similarity	NPD5226	Approved
0.69	Remote Similarity	NPD5224	Approved
0.69	Remote Similarity	NPD4633	Approved
0.6897	Remote Similarity	NPD5364	Discontinued
0.6867	Remote Similarity	NPD4691	Approved
0.6863	Remote Similarity	NPD6402	Approved
0.6863	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD5739	Approved
0.6863	Remote Similarity	NPD6675	Approved
0.686	Remote Similarity	NPD6933	Approved
0.6842	Remote Similarity	NPD5284	Approved
0.6842	Remote Similarity	NPD5281	Approved
0.6832	Remote Similarity	NPD5174	Approved
0.6832	Remote Similarity	NPD4754	Approved
0.6832	Remote Similarity	NPD5175	Approved
0.6829	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4785	Approved
0.6824	Remote Similarity	NPD4784	Approved
0.6824	Remote Similarity	NPD5733	Approved
0.6809	Remote Similarity	NPD6904	Approved
0.6809	Remote Similarity	NPD6080	Approved
0.6809	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD6412	Phase 2
0.6782	Remote Similarity	NPD5776	Phase 2
0.6782	Remote Similarity	NPD6925	Approved
0.6774	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6922	Approved
0.6747	Remote Similarity	NPD6923	Approved
0.6737	Remote Similarity	NPD4096	Approved
0.6731	Remote Similarity	NPD7320	Approved
0.6731	Remote Similarity	NPD6881	Approved
0.6731	Remote Similarity	NPD6899	Approved
0.6705	Remote Similarity	NPD7145	Approved
0.6703	Remote Similarity	NPD6695	Phase 3
0.6702	Remote Similarity	NPD5208	Approved
0.6701	Remote Similarity	NPD7900	Approved
0.6701	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4767	Approved
0.6699	Remote Similarity	NPD4768	Approved
0.6697	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6635	Remote Similarity	NPD5701	Approved
0.6635	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4058	Approved
0.6628	Remote Similarity	NPD4687	Approved
0.6604	Remote Similarity	NPD7290	Approved
0.6604	Remote Similarity	NPD7102	Approved
0.6604	Remote Similarity	NPD6883	Approved
0.6598	Remote Similarity	NPD5133	Approved
0.6588	Remote Similarity	NPD5276	Approved
0.6588	Remote Similarity	NPD7152	Approved
0.6588	Remote Similarity	NPD7151	Approved
0.6588	Remote Similarity	NPD7150	Approved
0.6574	Remote Similarity	NPD8133	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD5168	Approved
0.6571	Remote Similarity	NPD5128	Approved
0.6571	Remote Similarity	NPD4730	Approved
0.6571	Remote Similarity	NPD4729	Approved
0.6569	Remote Similarity	NPD7632	Discontinued
0.6559	Remote Similarity	NPD6893	Approved
0.6556	Remote Similarity	NPD7514	Phase 3
0.6552	Remote Similarity	NPD4190	Phase 3
0.6552	Remote Similarity	NPD5275	Approved
0.6548	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6847	Approved
0.6542	Remote Similarity	NPD6649	Approved
0.6542	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD8130	Phase 1
0.6542	Remote Similarity	NPD6869	Approved
0.6542	Remote Similarity	NPD6617	Approved
0.6535	Remote Similarity	NPD6404	Discontinued
0.6526	Remote Similarity	NPD4518	Approved
0.6522	Remote Similarity	NPD5362	Discontinued
0.6517	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6012	Approved
0.6509	Remote Similarity	NPD6013	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