NPASS Compound

Structure

CID68828 OpenBabel06191715402D 32 36 0 0 1 0 0 0 0 0999 V2000 5.7192 0.3464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1844 0.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4503 1.4227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 0.5707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0241 1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8705 -1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6450 2.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6445 0.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 1.4246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1113 -1.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6437 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4667 2.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8228 2.3733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8217 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2902 -1.8977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8228 -1.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -1.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7819 0.1976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1110 -0.4736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6448 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6439 0.9491 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9496 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4674 -0.4741 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4679 -2.3721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4662 1.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8222 1.4242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8225 -0.4746 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 2.4676 -1.4231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5654 -2.6657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1733 -3.0070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 30 1 0 0 0 0 20 19 1 6 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 21 28 1 6 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 30 1 1 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	7.649
LogD:	5.788
LogS:	-6.373
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	4.608
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
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:	-5.281
MDCK Permeability:	1.1316494237689767e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.375
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	94.57306671142578%
Volume Distribution (VD):	0.703
Pgp-substrate:	2.253039836883545%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.768
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.749
CYP3A4-inhibitor:	0.338
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	2.468
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.36
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.238
Skin Sensitization:	0.615
Carcinogencity:	0.044
Eye Corrosion:	0.858
Eye Irritation:	0.482
Respiratory Toxicity:	0.846

Download Data

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

Natural Product: NPC68828

Natural Product ID:	NPC68828
*Common Name:**	3-Deoxybetulonic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:	3-Deoxybetulonic Acid
Standard InCHIKey:	PTQVWLXNKDWNRD-INPVNEGFSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19(2)20-11-16-30(25(31)32)18-17-28(6)21(24(20)30)9-10-23-27(5)14-8-13-26(3,4)22(27)12-15-29(23,28)7/h20-24H,1,8-18H2,2-7H3,(H,31,32)/t20-,21+,22-,23+,24+,27-,28+,29+,30-/m0/s1
SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCCC1(C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517065
PubChem CID:	11070248
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
NPO1145	Coussarea paniculata	Species	Rubiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[12662105]
NPO1145	Coussarea paniculata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22190	Helichrysum candolleanum	Species	Asteraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	17.4	ug.mL-1	PMID[549473]

☑ 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 NPC68828 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	159
0.1-0.2	1821
0.2-0.3	11178
0.3-0.4	13125
0.4-0.5	6226
0.5-0.6	5366
0.6-0.7	3660
0.7-0.8	1010
0.8-0.85	90
0.85-0.9	46
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC192744
0.9583	High Similarity	NPC246445
0.9452	High Similarity	NPC66105
0.9437	High Similarity	NPC36310
0.9437	High Similarity	NPC330659
0.9437	High Similarity	NPC244708
0.9437	High Similarity	NPC161187
0.9221	High Similarity	NPC472740
0.9067	High Similarity	NPC63020
0.9041	High Similarity	NPC255168
0.8987	High Similarity	NPC264317
0.8987	High Similarity	NPC201655
0.8987	High Similarity	NPC294438
0.8947	High Similarity	NPC201459
0.8933	High Similarity	NPC471035
0.8933	High Similarity	NPC212661
0.8904	High Similarity	NPC279241
0.8875	High Similarity	NPC12774
0.8875	High Similarity	NPC2783
0.8816	High Similarity	NPC321690
0.88	High Similarity	NPC89294
0.88	High Similarity	NPC20466
0.8765	High Similarity	NPC33768
0.8765	High Similarity	NPC269360
0.8765	High Similarity	NPC264005
0.8734	High Similarity	NPC167103
0.8734	High Similarity	NPC245866
0.8718	High Similarity	NPC147066
0.8718	High Similarity	NPC474484
0.8718	High Similarity	NPC103754
0.8701	High Similarity	NPC16394
0.8701	High Similarity	NPC158846
0.8684	High Similarity	NPC471899
0.8684	High Similarity	NPC107039
0.8684	High Similarity	NPC471897
0.8659	High Similarity	NPC4309
0.8659	High Similarity	NPC16377
0.8659	High Similarity	NPC471900
0.8659	High Similarity	NPC474719
0.863	High Similarity	NPC108131
0.8611	High Similarity	NPC290445
0.8611	High Similarity	NPC36616
0.8592	High Similarity	NPC42060
0.8571	High Similarity	NPC280654
0.8571	High Similarity	NPC110094
0.8571	High Similarity	NPC260385
0.8554	High Similarity	NPC57954
0.8554	High Similarity	NPC271974
0.8554	High Similarity	NPC213832
0.8554	High Similarity	NPC220498
0.8554	High Similarity	NPC247312
0.85	High Similarity	NPC475726
0.85	High Similarity	NPC471037
0.85	High Similarity	NPC175410
0.85	High Similarity	NPC472743
0.8481	Intermediate Similarity	NPC267691
0.8481	Intermediate Similarity	NPC263272
0.8481	Intermediate Similarity	NPC38350
0.8481	Intermediate Similarity	NPC162632
0.8481	Intermediate Similarity	NPC201912
0.8481	Intermediate Similarity	NPC274050
0.8481	Intermediate Similarity	NPC232625
0.8462	Intermediate Similarity	NPC215843
0.8462	Intermediate Similarity	NPC199595
0.8462	Intermediate Similarity	NPC477371
0.8462	Intermediate Similarity	NPC231431
0.8452	Intermediate Similarity	NPC169933
0.8442	Intermediate Similarity	NPC238227
0.8415	Intermediate Similarity	NPC80590
0.8415	Intermediate Similarity	NPC70661
0.8395	Intermediate Similarity	NPC74595
0.8395	Intermediate Similarity	NPC263974
0.8395	Intermediate Similarity	NPC474482
0.8395	Intermediate Similarity	NPC475509
0.8395	Intermediate Similarity	NPC474233
0.8395	Intermediate Similarity	NPC475745
0.8395	Intermediate Similarity	NPC264665
0.8378	Intermediate Similarity	NPC91369
0.8375	Intermediate Similarity	NPC170985
0.8375	Intermediate Similarity	NPC69101
0.8375	Intermediate Similarity	NPC251779
0.8375	Intermediate Similarity	NPC260956
0.8375	Intermediate Similarity	NPC320514
0.8354	Intermediate Similarity	NPC37038
0.8354	Intermediate Similarity	NPC104545
0.8353	Intermediate Similarity	NPC471901
0.8353	Intermediate Similarity	NPC160506
0.8353	Intermediate Similarity	NPC475416
0.8333	Intermediate Similarity	NPC268736
0.8333	Intermediate Similarity	NPC477931
0.8313	Intermediate Similarity	NPC134197
0.8293	Intermediate Similarity	NPC98270
0.8293	Intermediate Similarity	NPC292553
0.8293	Intermediate Similarity	NPC29447
0.8272	Intermediate Similarity	NPC83569
0.8272	Intermediate Similarity	NPC200752
0.8272	Intermediate Similarity	NPC70834
0.8272	Intermediate Similarity	NPC69279
0.8267	Intermediate Similarity	NPC72343
0.8256	Intermediate Similarity	NPC291373
0.8256	Intermediate Similarity	NPC473690
0.8256	Intermediate Similarity	NPC471902
0.8256	Intermediate Similarity	NPC475061
0.8256	Intermediate Similarity	NPC224060
0.8256	Intermediate Similarity	NPC244356
0.8256	Intermediate Similarity	NPC287118
0.825	Intermediate Similarity	NPC471898
0.825	Intermediate Similarity	NPC221647
0.825	Intermediate Similarity	NPC142244
0.825	Intermediate Similarity	NPC477372
0.8243	Intermediate Similarity	NPC476734
0.8243	Intermediate Similarity	NPC252032
0.8243	Intermediate Similarity	NPC469941
0.8243	Intermediate Similarity	NPC319671
0.8228	Intermediate Similarity	NPC471475
0.8219	Intermediate Similarity	NPC474221
0.8219	Intermediate Similarity	NPC130459
0.8219	Intermediate Similarity	NPC478180
0.8214	Intermediate Similarity	NPC211162
0.8214	Intermediate Similarity	NPC146937
0.8214	Intermediate Similarity	NPC183374
0.8205	Intermediate Similarity	NPC106078
0.8193	Intermediate Similarity	NPC98236
0.8193	Intermediate Similarity	NPC269396
0.8193	Intermediate Similarity	NPC155011
0.8193	Intermediate Similarity	NPC472505
0.8193	Intermediate Similarity	NPC472738
0.8182	Intermediate Similarity	NPC192540
0.8182	Intermediate Similarity	NPC201027
0.8182	Intermediate Similarity	NPC279666
0.8171	Intermediate Similarity	NPC96095
0.8171	Intermediate Similarity	NPC194937
0.8171	Intermediate Similarity	NPC476038
0.8161	Intermediate Similarity	NPC277399
0.8161	Intermediate Similarity	NPC303863
0.8148	Intermediate Similarity	NPC145143
0.8148	Intermediate Similarity	NPC477858
0.8148	Intermediate Similarity	NPC133391
0.8133	Intermediate Similarity	NPC477929
0.8133	Intermediate Similarity	NPC235586
0.8125	Intermediate Similarity	NPC477057
0.8118	Intermediate Similarity	NPC116146
0.8118	Intermediate Similarity	NPC24772
0.8108	Intermediate Similarity	NPC473225
0.8095	Intermediate Similarity	NPC142361
0.8095	Intermediate Similarity	NPC4643
0.8095	Intermediate Similarity	NPC136948
0.8095	Intermediate Similarity	NPC96496
0.8095	Intermediate Similarity	NPC57469
0.8095	Intermediate Similarity	NPC474684
0.8082	Intermediate Similarity	NPC43300
0.8077	Intermediate Similarity	NPC69143
0.8077	Intermediate Similarity	NPC476601
0.8077	Intermediate Similarity	NPC104806
0.8072	Intermediate Similarity	NPC269638
0.8072	Intermediate Similarity	NPC283733
0.8052	Intermediate Similarity	NPC283908
0.8052	Intermediate Similarity	NPC18819
0.8052	Intermediate Similarity	NPC103958
0.8052	Intermediate Similarity	NPC161923
0.8052	Intermediate Similarity	NPC251970
0.8052	Intermediate Similarity	NPC183503
0.8052	Intermediate Similarity	NPC46610
0.8052	Intermediate Similarity	NPC241854
0.8052	Intermediate Similarity	NPC476046
0.8049	Intermediate Similarity	NPC477852
0.8049	Intermediate Similarity	NPC215893
0.8049	Intermediate Similarity	NPC168188
0.8049	Intermediate Similarity	NPC470015
0.8049	Intermediate Similarity	NPC477373
0.8049	Intermediate Similarity	NPC5280
0.8026	Intermediate Similarity	NPC469940
0.8026	Intermediate Similarity	NPC160817
0.8	Intermediate Similarity	NPC118987
0.8	Intermediate Similarity	NPC196827
0.8	Intermediate Similarity	NPC472739
0.8	Intermediate Similarity	NPC474962
0.8	Intermediate Similarity	NPC255176
0.8	Intermediate Similarity	NPC274996
0.8	Intermediate Similarity	NPC196197
0.8	Intermediate Similarity	NPC64466
0.7976	Intermediate Similarity	NPC186975
0.7976	Intermediate Similarity	NPC55309
0.7976	Intermediate Similarity	NPC187545
0.7976	Intermediate Similarity	NPC28252
0.7976	Intermediate Similarity	NPC475007
0.7975	Intermediate Similarity	NPC143133
0.7975	Intermediate Similarity	NPC298168
0.7952	Intermediate Similarity	NPC164577
0.7952	Intermediate Similarity	NPC472864
0.7952	Intermediate Similarity	NPC156981
0.7952	Intermediate Similarity	NPC165064
0.7952	Intermediate Similarity	NPC19849
0.7952	Intermediate Similarity	NPC248758
0.7952	Intermediate Similarity	NPC477289
0.7949	Intermediate Similarity	NPC476844
0.7907	Intermediate Similarity	NPC474704
0.7907	Intermediate Similarity	NPC262043
0.7907	Intermediate Similarity	NPC475921
0.7907	Intermediate Similarity	NPC474570

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 NPC68828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2244
0.2-0.3	4350
0.3-0.4	1573
0.4-0.5	414
0.5-0.6	196
0.6-0.7	145
0.7-0.8	62
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8987	High Similarity	NPD7520	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD8034	Phase 2
0.8353	Intermediate Similarity	NPD8035	Phase 2
0.8082	Intermediate Similarity	NPD4224	Phase 2
0.8049	Intermediate Similarity	NPD4788	Approved
0.8026	Intermediate Similarity	NPD6081	Approved
0.7821	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4786	Approved
0.7711	Intermediate Similarity	NPD4223	Phase 3
0.7711	Intermediate Similarity	NPD4221	Approved
0.7647	Intermediate Similarity	NPD5329	Approved
0.764	Intermediate Similarity	NPD6399	Phase 3
0.7632	Intermediate Similarity	NPD5360	Phase 3
0.7632	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6117	Approved
0.7586	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6098	Approved
0.7531	Intermediate Similarity	NPD6116	Phase 1
0.7529	Intermediate Similarity	NPD4197	Approved
0.7528	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD3667	Approved
0.7439	Intermediate Similarity	NPD6697	Approved
0.7439	Intermediate Similarity	NPD6118	Approved
0.7439	Intermediate Similarity	NPD6115	Approved
0.7439	Intermediate Similarity	NPD6114	Approved
0.7439	Intermediate Similarity	NPD3617	Approved
0.7436	Intermediate Similarity	NPD4789	Approved
0.7386	Intermediate Similarity	NPD5737	Approved
0.7386	Intermediate Similarity	NPD6672	Approved
0.7363	Intermediate Similarity	NPD7748	Approved
0.7356	Intermediate Similarity	NPD5205	Approved
0.7356	Intermediate Similarity	NPD6684	Approved
0.7356	Intermediate Similarity	NPD4690	Approved
0.7356	Intermediate Similarity	NPD6409	Approved
0.7356	Intermediate Similarity	NPD7146	Approved
0.7356	Intermediate Similarity	NPD5330	Approved
0.7356	Intermediate Similarity	NPD4689	Approved
0.7356	Intermediate Similarity	NPD4138	Approved
0.7356	Intermediate Similarity	NPD7521	Approved
0.7356	Intermediate Similarity	NPD7334	Approved
0.7356	Intermediate Similarity	NPD4693	Phase 3
0.7356	Intermediate Similarity	NPD4688	Approved
0.7342	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5284	Approved
0.7333	Intermediate Similarity	NPD5281	Approved
0.7326	Intermediate Similarity	NPD3665	Phase 1
0.7326	Intermediate Similarity	NPD3133	Approved
0.7326	Intermediate Similarity	NPD3666	Approved
0.7312	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD6084	Phase 2
0.7303	Intermediate Similarity	NPD6080	Approved
0.7303	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6904	Approved
0.7303	Intermediate Similarity	NPD5328	Approved
0.7303	Intermediate Similarity	NPD6673	Approved
0.7284	Intermediate Similarity	NPD3702	Approved
0.7237	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4245	Approved
0.7215	Intermediate Similarity	NPD4244	Approved
0.7191	Intermediate Similarity	NPD6903	Approved
0.7191	Intermediate Similarity	NPD5208	Approved
0.7176	Intermediate Similarity	NPD4139	Approved
0.7176	Intermediate Similarity	NPD4692	Approved
0.7159	Intermediate Similarity	NPD4694	Approved
0.7159	Intermediate Similarity	NPD3618	Phase 1
0.7159	Intermediate Similarity	NPD5280	Approved
0.7159	Intermediate Similarity	NPD5690	Phase 2
0.7143	Intermediate Similarity	NPD6079	Approved
0.7128	Intermediate Similarity	NPD7902	Approved
0.7125	Intermediate Similarity	NPD5777	Approved
0.7125	Intermediate Similarity	NPD4758	Discontinued
0.7125	Intermediate Similarity	NPD4243	Approved
0.7111	Intermediate Similarity	NPD4753	Phase 2
0.7097	Intermediate Similarity	NPD5695	Phase 3
0.7089	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3698	Phase 2
0.7089	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD4747	Approved
0.6979	Remote Similarity	NPD6404	Discontinued
0.6966	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5279	Phase 3
0.6957	Remote Similarity	NPD6050	Approved
0.6957	Remote Similarity	NPD5693	Phase 1
0.6951	Remote Similarity	NPD4784	Approved
0.6951	Remote Similarity	NPD4785	Approved
0.6941	Remote Similarity	NPD4195	Approved
0.6932	Remote Similarity	NPD3668	Phase 3
0.6915	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4202	Approved
0.6875	Remote Similarity	NPD7638	Approved
0.6875	Remote Similarity	NPD4137	Phase 3
0.6867	Remote Similarity	NPD7339	Approved
0.6867	Remote Similarity	NPD6942	Approved
0.686	Remote Similarity	NPD4695	Discontinued
0.686	Remote Similarity	NPD7525	Registered
0.6848	Remote Similarity	NPD5207	Approved
0.6848	Remote Similarity	NPD5692	Phase 3
0.6842	Remote Similarity	NPD7614	Phase 1
0.6824	Remote Similarity	NPD5364	Discontinued
0.6809	Remote Similarity	NPD6001	Approved
0.6809	Remote Similarity	NPD7900	Approved
0.6809	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7639	Approved
0.6804	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD6402	Approved
0.68	Remote Similarity	NPD6675	Approved
0.68	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD7128	Approved
0.679	Remote Similarity	NPD4691	Approved
0.6778	Remote Similarity	NPD4519	Discontinued
0.6778	Remote Similarity	NPD4623	Approved
0.6774	Remote Similarity	NPD5694	Approved
0.675	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5733	Approved
0.6737	Remote Similarity	NPD4629	Approved
0.6737	Remote Similarity	NPD5210	Approved
0.6705	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD4096	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD5275	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6628	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6372	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.6598	Remote Similarity	NPD5173	Approved
0.6598	Remote Similarity	NPD4755	Approved
0.6588	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5697	Approved
0.6569	Remote Similarity	NPD5701	Approved
0.6552	Remote Similarity	NPD7645	Phase 2
0.6548	Remote Similarity	NPD4058	Approved
0.6548	Remote Similarity	NPD4687	Approved
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6526	Remote Similarity	NPD5133	Approved
0.6509	Remote Similarity	NPD8133	Approved
0.6506	Remote Similarity	NPD5276	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6617	Approved
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD8130	Phase 1
0.6465	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD4700	Approved
0.6465	Remote Similarity	NPD5286	Approved
0.6452	Remote Similarity	NPD4518	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD3671	Phase 1
0.6436	Remote Similarity	NPD6052	Approved
0.6415	Remote Similarity	NPD6882	Approved
0.6415	Remote Similarity	NPD8297	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.64	Remote Similarity	NPD5223	Approved
0.6395	Remote Similarity	NPD6933	Approved
0.6392	Remote Similarity	NPD5654	Approved
0.6383	Remote Similarity	NPD6051	Approved
0.6337	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD7632	Discontinued
0.6337	Remote Similarity	NPD5211	Phase 2
0.6337	Remote Similarity	NPD5091	Approved
0.6337	Remote Similarity	NPD4633	Approved
0.6337	Remote Similarity	NPD5225	Approved
0.633	Remote Similarity	NPD7115	Discovery
0.6327	Remote Similarity	NPD7732	Phase 3
0.6275	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD4754	Approved
0.6275	Remote Similarity	NPD5175	Approved
0.6265	Remote Similarity	NPD6922	Approved
0.6265	Remote Similarity	NPD6923	Approved
0.6264	Remote Similarity	NPD5362	Discontinued
0.6263	Remote Similarity	NPD5959	Approved
0.625	Remote Similarity	NPD6614	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.6239	Remote Similarity	NPD6868	Approved
0.6222	Remote Similarity	NPD857	Phase 3
0.6214	Remote Similarity	NPD5141	Approved
0.6204	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD7143	Approved
0.619	Remote Similarity	NPD7144	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