NPASS Compound

Structure

CID70982 OpenBabel06191715412D 33 37 0 0 1 0 0 0 0 0999 V2000 -0.0738 5.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2777 3.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8355 5.7479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 -2.9632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5656 -2.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 1.9856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6922 -1.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1870 4.0943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8854 3.1661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3833 0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5372 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3833 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4931 2.6437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5793 4.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5339 4.8196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5384 2.4408 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5384 1.4648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8461 -1.4655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8461 -0.4885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5372 -1.4654 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6917 -1.9539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 0.9764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6922 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8461 -0.4885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7947 3.5719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4033 -1.9653 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 3 21 2 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 30 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 22 9 1 1 0 0 0 22 23 1 0 0 0 0 23 28 1 1 0 0 0 24 27 1 0 0 0 0 24 30 1 1 0 0 0 25 29 1 6 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 33 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 6 0 0 0 30 31 1 6 0 0 0 31 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	230.12
Volume:	223.014
LogP:	0.548
LogD:	0.831
LogS:	-0.456
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	4.504
Fsp3:	0.909
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.042
MDCK Permeability:	0.00025845388881862164
Pgp-inhibitor:	0.001
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	12.684938430786133%
Volume Distribution (VD):	0.565
Pgp-substrate:	80.29419708251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.868
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	12.779
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.494
Carcinogencity:	0.271
Eye Corrosion:	0.768
Eye Irritation:	0.901
Respiratory Toxicity:	0.595

Download Data

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

Natural Product: NPC70982

Natural Product ID:	NPC70982
*Common Name:**	FJXNINQGUTYPNE-DLJSKDEVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FJXNINQGUTYPNE-DLJSKDEVSA-N
Standard InCHI:	InChI=1S/C31H52O2/c1-20(2)21(3)8-9-22(18-32)23-12-14-29(7)25-11-10-24-27(4,5)26(33)13-15-30(24)19-31(25,30)17-16-28(23,29)6/h20,22-26,32-33H,3,8-19H2,1-2,4-7H3/t22-,23+,24-,25-,26-,28+,29-,30+,31-/m0/s1
SMILES:	CC(C)C(=C)CC[C@@H](CO)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2331820
PubChem CID:	71716352
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	Cupules	n.a.	n.a.	PMID[25098388]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26308	Lithocarpus polystachyus	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[451777]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[451777]

☑ 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 NPC70982 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	171
0.1-0.2	2274
0.2-0.3	12619
0.3-0.4	12831
0.4-0.5	5290
0.5-0.6	5208
0.6-0.7	3093
0.7-0.8	977
0.8-0.85	128
0.85-0.9	81
0.9-0.95	13
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230704
0.9855	High Similarity	NPC145552
0.9855	High Similarity	NPC5046
0.9855	High Similarity	NPC254509
0.9855	High Similarity	NPC49168
0.9855	High Similarity	NPC196358
0.9718	High Similarity	NPC331618
0.9718	High Similarity	NPC257191
0.9714	High Similarity	NPC200243
0.971	High Similarity	NPC195489
0.9583	High Similarity	NPC472342
0.9565	High Similarity	NPC111234
0.9437	High Similarity	NPC212879
0.9437	High Similarity	NPC178383
0.9437	High Similarity	NPC231256
0.9437	High Similarity	NPC185536
0.9437	High Similarity	NPC104387
0.9437	High Similarity	NPC3403
0.9437	High Similarity	NPC240235
0.942	High Similarity	NPC45296
0.9315	High Similarity	NPC65897
0.9315	High Similarity	NPC85346
0.9315	High Similarity	NPC302041
0.9306	High Similarity	NPC86305
0.9306	High Similarity	NPC93662
0.9306	High Similarity	NPC278091
0.9306	High Similarity	NPC78067
0.9306	High Similarity	NPC14112
0.9306	High Similarity	NPC91573
0.9296	High Similarity	NPC472503
0.9296	High Similarity	NPC62657
0.9296	High Similarity	NPC308440
0.9296	High Similarity	NPC25511
0.9296	High Similarity	NPC192638
0.9178	High Similarity	NPC248830
0.9178	High Similarity	NPC119355
0.9178	High Similarity	NPC212241
0.9178	High Similarity	NPC202540
0.9054	High Similarity	NPC312328
0.9054	High Similarity	NPC477819
0.9054	High Similarity	NPC138621
0.9054	High Similarity	NPC6978
0.9054	High Similarity	NPC31828
0.9054	High Similarity	NPC102708
0.9054	High Similarity	NPC301707
0.9054	High Similarity	NPC167037
0.9054	High Similarity	NPC42853
0.9054	High Similarity	NPC477817
0.9054	High Similarity	NPC285761
0.9054	High Similarity	NPC244385
0.9041	High Similarity	NPC237460
0.8961	High Similarity	NPC113978
0.8933	High Similarity	NPC80297
0.8933	High Similarity	NPC49627
0.8933	High Similarity	NPC475727
0.8933	High Similarity	NPC49599
0.8933	High Similarity	NPC472742
0.8933	High Similarity	NPC273410
0.8933	High Similarity	NPC116119
0.8933	High Similarity	NPC80530
0.8919	High Similarity	NPC138502
0.8919	High Similarity	NPC260301
0.8919	High Similarity	NPC307336
0.8904	High Similarity	NPC103822
0.8816	High Similarity	NPC71535
0.8816	High Similarity	NPC78545
0.8816	High Similarity	NPC322313
0.8816	High Similarity	NPC475679
0.8816	High Similarity	NPC102253
0.8816	High Similarity	NPC236237
0.8816	High Similarity	NPC13554
0.88	High Similarity	NPC472500
0.88	High Similarity	NPC472501
0.88	High Similarity	NPC472499
0.8784	High Similarity	NPC38141
0.8784	High Similarity	NPC73875
0.8784	High Similarity	NPC189883
0.8767	High Similarity	NPC476736
0.8734	High Similarity	NPC76518
0.8718	High Similarity	NPC82623
0.8718	High Similarity	NPC134481
0.8714	High Similarity	NPC473230
0.8714	High Similarity	NPC475884
0.8696	High Similarity	NPC473276
0.8696	High Similarity	NPC41577
0.8696	High Similarity	NPC476737
0.8696	High Similarity	NPC474380
0.8696	High Similarity	NPC27243
0.8684	High Similarity	NPC24504
0.8684	High Similarity	NPC476316
0.8684	High Similarity	NPC1319
0.8667	High Similarity	NPC214570
0.8667	High Similarity	NPC34019
0.8649	High Similarity	NPC141071
0.8649	High Similarity	NPC322353
0.8649	High Similarity	NPC121744
0.8649	High Similarity	NPC118508
0.8649	High Similarity	NPC471723
0.8649	High Similarity	NPC257347
0.863	High Similarity	NPC472506
0.863	High Similarity	NPC211009
0.8625	High Similarity	NPC269058
0.8625	High Similarity	NPC71520
0.8608	High Similarity	NPC86238
0.859	High Similarity	NPC477599
0.859	High Similarity	NPC296701
0.859	High Similarity	NPC218616
0.8571	High Similarity	NPC236112
0.8571	High Similarity	NPC47149
0.8571	High Similarity	NPC206735
0.8553	High Similarity	NPC275910
0.8553	High Similarity	NPC472502
0.8553	High Similarity	NPC475
0.8551	High Similarity	NPC69149
0.8533	High Similarity	NPC321381
0.8533	High Similarity	NPC300324
0.8533	High Similarity	NPC240604
0.8533	High Similarity	NPC134330
0.8533	High Similarity	NPC129165
0.8533	High Similarity	NPC202642
0.8533	High Similarity	NPC46160
0.8533	High Similarity	NPC107059
0.8533	High Similarity	NPC321016
0.8519	High Similarity	NPC89747
0.85	High Similarity	NPC22133
0.8493	Intermediate Similarity	NPC164045
0.8493	Intermediate Similarity	NPC301226
0.8481	Intermediate Similarity	NPC211135
0.8481	Intermediate Similarity	NPC216420
0.8481	Intermediate Similarity	NPC470929
0.8481	Intermediate Similarity	NPC207013
0.8481	Intermediate Similarity	NPC5280
0.8481	Intermediate Similarity	NPC232023
0.8481	Intermediate Similarity	NPC477818
0.8481	Intermediate Similarity	NPC472743
0.8481	Intermediate Similarity	NPC85095
0.8481	Intermediate Similarity	NPC110778
0.8481	Intermediate Similarity	NPC475726
0.8481	Intermediate Similarity	NPC246956
0.8472	Intermediate Similarity	NPC210323
0.8472	Intermediate Similarity	NPC470830
0.8472	Intermediate Similarity	NPC241085
0.8472	Intermediate Similarity	NPC299948
0.8462	Intermediate Similarity	NPC157655
0.8462	Intermediate Similarity	NPC474531
0.8442	Intermediate Similarity	NPC30986
0.8442	Intermediate Similarity	NPC209430
0.8442	Intermediate Similarity	NPC5604
0.8442	Intermediate Similarity	NPC47808
0.8442	Intermediate Similarity	NPC472463
0.8421	Intermediate Similarity	NPC318495
0.8421	Intermediate Similarity	NPC198968
0.8421	Intermediate Similarity	NPC155986
0.8415	Intermediate Similarity	NPC67872
0.8415	Intermediate Similarity	NPC146937
0.8406	Intermediate Similarity	NPC114891
0.84	Intermediate Similarity	NPC285893
0.84	Intermediate Similarity	NPC28657
0.84	Intermediate Similarity	NPC136188
0.84	Intermediate Similarity	NPC304309
0.84	Intermediate Similarity	NPC230301
0.84	Intermediate Similarity	NPC22105
0.84	Intermediate Similarity	NPC162742
0.84	Intermediate Similarity	NPC144075
0.84	Intermediate Similarity	NPC288035
0.84	Intermediate Similarity	NPC134847
0.8395	Intermediate Similarity	NPC94462
0.8378	Intermediate Similarity	NPC201373
0.8375	Intermediate Similarity	NPC474482
0.8375	Intermediate Similarity	NPC264665
0.8375	Intermediate Similarity	NPC475745
0.8375	Intermediate Similarity	NPC74595
0.8375	Intermediate Similarity	NPC255882
0.8375	Intermediate Similarity	NPC209802
0.8354	Intermediate Similarity	NPC470049
0.8354	Intermediate Similarity	NPC477858
0.8354	Intermediate Similarity	NPC248886
0.8354	Intermediate Similarity	NPC30166
0.8354	Intermediate Similarity	NPC472504
0.8333	Intermediate Similarity	NPC2648
0.8312	Intermediate Similarity	NPC186191
0.8312	Intermediate Similarity	NPC477522
0.8312	Intermediate Similarity	NPC474216
0.8312	Intermediate Similarity	NPC473943
0.8312	Intermediate Similarity	NPC87604
0.8312	Intermediate Similarity	NPC205455
0.831	Intermediate Similarity	NPC142712
0.8289	Intermediate Similarity	NPC113733
0.8289	Intermediate Similarity	NPC470362
0.8286	Intermediate Similarity	NPC144650
0.8286	Intermediate Similarity	NPC219940
0.8286	Intermediate Similarity	NPC101128
0.8272	Intermediate Similarity	NPC292553
0.8272	Intermediate Similarity	NPC294438
0.8272	Intermediate Similarity	NPC264317
0.8267	Intermediate Similarity	NPC100334
0.8267	Intermediate Similarity	NPC469593
0.8267	Intermediate Similarity	NPC469533
0.8267	Intermediate Similarity	NPC469534
0.8261	Intermediate Similarity	NPC71460

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 NPC70982 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	2588
0.2-0.3	4402
0.3-0.4	1400
0.4-0.5	243
0.5-0.6	153
0.6-0.7	157
0.7-0.8	41
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8816	High Similarity	NPD7525	Registered
0.84	Intermediate Similarity	NPD7339	Approved
0.84	Intermediate Similarity	NPD6942	Approved
0.8272	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7645	Phase 2
0.7973	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6924	Approved
0.7792	Intermediate Similarity	NPD6926	Approved
0.7711	Intermediate Similarity	NPD4786	Approved
0.7674	Intermediate Similarity	NPD5328	Approved
0.7632	Intermediate Similarity	NPD4787	Phase 1
0.7595	Intermediate Similarity	NPD6933	Approved
0.759	Intermediate Similarity	NPD4788	Approved
0.7532	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7152	Approved
0.7532	Intermediate Similarity	NPD7151	Approved
0.7532	Intermediate Similarity	NPD7150	Approved
0.7532	Intermediate Similarity	NPD4243	Approved
0.7532	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD6922	Approved
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD6923	Approved
0.747	Intermediate Similarity	NPD3667	Approved
0.7439	Intermediate Similarity	NPD4748	Discontinued
0.7403	Intermediate Similarity	NPD7144	Approved
0.7403	Intermediate Similarity	NPD7143	Approved
0.7375	Intermediate Similarity	NPD6117	Approved
0.7342	Intermediate Similarity	NPD4784	Approved
0.7342	Intermediate Similarity	NPD4785	Approved
0.7342	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6929	Approved
0.7284	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6931	Approved
0.7229	Intermediate Similarity	NPD6930	Phase 2
0.7229	Intermediate Similarity	NPD7509	Discontinued
0.7222	Intermediate Similarity	NPD4202	Approved
0.7195	Intermediate Similarity	NPD6114	Approved
0.7195	Intermediate Similarity	NPD6697	Approved
0.7195	Intermediate Similarity	NPD6118	Approved
0.7195	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD6902	Approved
0.7093	Intermediate Similarity	NPD3133	Approved
0.7093	Intermediate Similarity	NPD3666	Approved
0.7093	Intermediate Similarity	NPD3665	Phase 1
0.7073	Intermediate Similarity	NPD5776	Phase 2
0.7073	Intermediate Similarity	NPD6932	Approved
0.7073	Intermediate Similarity	NPD6925	Approved
0.7037	Intermediate Similarity	NPD5275	Approved
0.7037	Intermediate Similarity	NPD3703	Phase 2
0.7037	Intermediate Similarity	NPD4190	Phase 3
0.7021	Intermediate Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD5221	Approved
0.6989	Remote Similarity	NPD5222	Approved
0.6989	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4697	Phase 3
0.6988	Remote Similarity	NPD7145	Approved
0.6977	Remote Similarity	NPD6695	Phase 3
0.6962	Remote Similarity	NPD4245	Approved
0.6962	Remote Similarity	NPD4244	Approved
0.6962	Remote Similarity	NPD4789	Approved
0.6947	Remote Similarity	NPD7639	Approved
0.6947	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5360	Phase 3
0.6923	Remote Similarity	NPD7515	Phase 2
0.6915	Remote Similarity	NPD5173	Approved
0.6915	Remote Similarity	NPD4755	Approved
0.6905	Remote Similarity	NPD6683	Phase 2
0.6905	Remote Similarity	NPD4195	Approved
0.6897	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6399	Phase 3
0.6835	Remote Similarity	NPD3698	Phase 2
0.6824	Remote Similarity	NPD7514	Phase 3
0.6824	Remote Similarity	NPD6928	Phase 2
0.6818	Remote Similarity	NPD6893	Approved
0.6786	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4696	Approved
0.6771	Remote Similarity	NPD5285	Approved
0.6771	Remote Similarity	NPD5286	Approved
0.6771	Remote Similarity	NPD4700	Approved
0.6753	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5279	Phase 3
0.6705	Remote Similarity	NPD3668	Phase 3
0.6703	Remote Similarity	NPD4753	Phase 2
0.6701	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD7524	Approved
0.6633	Remote Similarity	NPD5226	Approved
0.6633	Remote Similarity	NPD5224	Approved
0.6633	Remote Similarity	NPD5211	Phase 2
0.6633	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD4633	Approved
0.6629	Remote Similarity	NPD5329	Approved
0.6628	Remote Similarity	NPD7332	Phase 2
0.6627	Remote Similarity	NPD8264	Approved
0.66	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD7128	Approved
0.66	Remote Similarity	NPD6675	Approved
0.66	Remote Similarity	NPD5739	Approved
0.6596	Remote Similarity	NPD7748	Approved
0.6588	Remote Similarity	NPD3671	Phase 1
0.6566	Remote Similarity	NPD5174	Approved
0.6566	Remote Similarity	NPD4754	Approved
0.6566	Remote Similarity	NPD5175	Approved
0.6552	Remote Similarity	NPD6898	Phase 1
0.6517	Remote Similarity	NPD4197	Approved
0.65	Remote Similarity	NPD6705	Phase 1
0.65	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6465	Remote Similarity	NPD7632	Discontinued
0.6463	Remote Similarity	NPD4758	Discontinued
0.6436	Remote Similarity	NPD4768	Approved
0.6436	Remote Similarity	NPD4767	Approved
0.6413	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD6372	Approved
0.6395	Remote Similarity	NPD3617	Approved
0.6392	Remote Similarity	NPD7902	Approved
0.6392	Remote Similarity	NPD6084	Phase 2
0.6392	Remote Similarity	NPD6083	Phase 2
0.6383	Remote Similarity	NPD7087	Discontinued
0.6374	Remote Similarity	NPD7146	Approved
0.6374	Remote Similarity	NPD5205	Approved
0.6374	Remote Similarity	NPD7521	Approved
0.6374	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5330	Approved
0.6374	Remote Similarity	NPD4690	Approved
0.6374	Remote Similarity	NPD4688	Approved
0.6374	Remote Similarity	NPD4693	Phase 3
0.6374	Remote Similarity	NPD4138	Approved
0.6374	Remote Similarity	NPD7334	Approved
0.6374	Remote Similarity	NPD6409	Approved
0.6374	Remote Similarity	NPD4689	Approved
0.6374	Remote Similarity	NPD6684	Approved
0.6373	Remote Similarity	NPD5697	Approved
0.6373	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD4159	Approved
0.6354	Remote Similarity	NPD5210	Approved
0.6354	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4629	Approved
0.6346	Remote Similarity	NPD7290	Approved
0.6346	Remote Similarity	NPD7102	Approved
0.6346	Remote Similarity	NPD6883	Approved
0.6344	Remote Similarity	NPD6051	Approved
0.6311	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD5168	Approved
0.6311	Remote Similarity	NPD5128	Approved
0.6311	Remote Similarity	NPD4730	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.6286	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD6617	Approved
0.6286	Remote Similarity	NPD8130	Phase 1
0.6277	Remote Similarity	NPD6700	Approved
0.6277	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6081	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD4224	Phase 2
0.625	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD4723	Approved
0.6237	Remote Similarity	NPD6903	Approved
0.6237	Remote Similarity	NPD6672	Approved
0.6237	Remote Similarity	NPD4722	Approved
0.6237	Remote Similarity	NPD5737	Approved
0.6232	Remote Similarity	NPD384	Approved
0.6232	Remote Similarity	NPD385	Approved
0.6226	Remote Similarity	NPD8297	Approved
0.6226	Remote Similarity	NPD6882	Approved
0.6211	Remote Similarity	NPD6703	Approved
0.6211	Remote Similarity	NPD6702	Approved
0.6207	Remote Similarity	NPD5364	Discontinued
0.6196	Remote Similarity	NPD5690	Phase 2
0.6196	Remote Similarity	NPD4694	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD5248	Approved
0.619	Remote Similarity	NPD4634	Approved
0.619	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD5250	Approved
0.618	Remote Similarity	NPD4139	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