NPASS Compound

Structure

NPC472342 OpenBabel07101718232D 33 37 0 0 1 0 0 0 0 0999 V2000 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1345 1.9057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1834 2.2147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9266 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9047 3.0917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 21 2 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 25 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 19 30 1 0 0 0 0 19 31 1 0 0 0 0 20 1 1 1 0 0 0 20 22 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 6 0 0 0 23 26 1 0 0 0 0 23 30 1 6 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 27 33 1 0 0 0 0 28 29 1 6 0 0 0 29 8 1 1 0 0 0 30 31 1 1 0 0 0 31 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.4
Volume:	516.894
LogP:	6.773
LogD:	5.066
LogS:	-5.193
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	5.608
Fsp3:	0.935
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:	-5.026
MDCK Permeability:	1.1999853995803278e-05
Pgp-inhibitor:	0.163
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.929
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	92.84716796875%
Volume Distribution (VD):	1.127
Pgp-substrate:	2.0068812370300293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.366
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.531
CYP3A4-inhibitor:	0.843
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	6.924
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.931
Carcinogencity:	0.098
Eye Corrosion:	0.318
Eye Irritation:	0.093
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC472342

Natural Product ID:	NPC472342
*Common Name:**	WXYNTJQRYPFIJD-CHIINMNOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WXYNTJQRYPFIJD-CHIINMNOSA-N
Standard InCHI:	InChI=1S/C31H52O2/c1-20(9-10-21(2)27(5,6)33)22-13-15-29(8)24-12-11-23-26(3,4)25(32)14-16-30(23)19-31(24,30)18-17-28(22,29)7/h20,22-25,32-33H,2,9-19H2,1,3-8H3/t20-,22-,23+,24+,25+,28-,29+,30-,31+/m1/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)CCC(=C)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359356
PubChem CID:	n.a.
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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ratio	=	4.0	n.a.	PMID[529642]

☑ 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 NPC472342 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	172
0.1-0.2	2179
0.2-0.3	10694
0.3-0.4	14221
0.4-0.5	5668
0.5-0.6	5425
0.6-0.7	3241
0.7-0.8	896
0.8-0.85	110
0.85-0.9	69
0.9-0.95	17
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC257191
0.9861	High Similarity	NPC331618
0.9583	High Similarity	NPC185536
0.9583	High Similarity	NPC230704
0.9583	High Similarity	NPC70982
0.9459	High Similarity	NPC301707
0.9444	High Similarity	NPC254509
0.9444	High Similarity	NPC196358
0.9444	High Similarity	NPC145552
0.9444	High Similarity	NPC5046
0.9444	High Similarity	NPC49168
0.9324	High Similarity	NPC119355
0.9324	High Similarity	NPC248830
0.9324	High Similarity	NPC212241
0.9315	High Similarity	NPC3403
0.9315	High Similarity	NPC200243
0.9306	High Similarity	NPC195489
0.92	High Similarity	NPC472501
0.9189	High Similarity	NPC91573
0.9178	High Similarity	NPC476736
0.9167	High Similarity	NPC111234
0.9103	High Similarity	NPC82623
0.9067	High Similarity	NPC307336
0.9067	High Similarity	NPC138502
0.9067	High Similarity	NPC260301
0.9054	High Similarity	NPC104387
0.9054	High Similarity	NPC240235
0.9054	High Similarity	NPC231256
0.9054	High Similarity	NPC178383
0.9054	High Similarity	NPC212879
0.9028	High Similarity	NPC45296
0.8974	High Similarity	NPC296701
0.8974	High Similarity	NPC218616
0.8947	High Similarity	NPC42853
0.8947	High Similarity	NPC302041
0.8947	High Similarity	NPC85346
0.8947	High Similarity	NPC285761
0.8947	High Similarity	NPC472499
0.8947	High Similarity	NPC472500
0.8947	High Similarity	NPC65897
0.8947	High Similarity	NPC31828
0.8933	High Similarity	NPC93662
0.8933	High Similarity	NPC278091
0.8933	High Similarity	NPC86305
0.8933	High Similarity	NPC38141
0.8933	High Similarity	NPC14112
0.8933	High Similarity	NPC78067
0.8919	High Similarity	NPC192638
0.8919	High Similarity	NPC62657
0.8919	High Similarity	NPC472503
0.8919	High Similarity	NPC308440
0.8919	High Similarity	NPC25511
0.8861	High Similarity	NPC134481
0.8831	High Similarity	NPC80530
0.8831	High Similarity	NPC24504
0.8831	High Similarity	NPC476316
0.8831	High Similarity	NPC49599
0.8831	High Similarity	NPC49627
0.8831	High Similarity	NPC273410
0.8816	High Similarity	NPC202540
0.8784	High Similarity	NPC472506
0.8718	High Similarity	NPC47149
0.8718	High Similarity	NPC102253
0.8718	High Similarity	NPC13554
0.8718	High Similarity	NPC236237
0.8718	High Similarity	NPC322313
0.8701	High Similarity	NPC477819
0.8701	High Similarity	NPC102708
0.8701	High Similarity	NPC244385
0.8701	High Similarity	NPC475
0.8701	High Similarity	NPC312328
0.8701	High Similarity	NPC6978
0.8701	High Similarity	NPC138621
0.8701	High Similarity	NPC167037
0.8701	High Similarity	NPC477817
0.8701	High Similarity	NPC472502
0.8684	High Similarity	NPC237460
0.8649	High Similarity	NPC164045
0.8625	High Similarity	NPC113978
0.8608	High Similarity	NPC157655
0.859	High Similarity	NPC5604
0.859	High Similarity	NPC209430
0.859	High Similarity	NPC116119
0.859	High Similarity	NPC475727
0.859	High Similarity	NPC472742
0.859	High Similarity	NPC80297
0.859	High Similarity	NPC30986
0.8571	High Similarity	NPC470758
0.8571	High Similarity	NPC470711
0.8554	High Similarity	NPC67872
0.8553	High Similarity	NPC144075
0.8553	High Similarity	NPC103822
0.8519	High Similarity	NPC474047
0.8519	High Similarity	NPC86238
0.85	High Similarity	NPC87489
0.85	High Similarity	NPC49964
0.85	High Similarity	NPC477858
0.8481	Intermediate Similarity	NPC164840
0.8481	Intermediate Similarity	NPC206735
0.8481	Intermediate Similarity	NPC78545
0.8481	Intermediate Similarity	NPC241290
0.8481	Intermediate Similarity	NPC71535
0.8481	Intermediate Similarity	NPC475679
0.8481	Intermediate Similarity	NPC209944
0.8462	Intermediate Similarity	NPC474216
0.8442	Intermediate Similarity	NPC73875
0.8442	Intermediate Similarity	NPC189883
0.8442	Intermediate Similarity	NPC470749
0.8421	Intermediate Similarity	NPC469533
0.8421	Intermediate Similarity	NPC469534
0.8421	Intermediate Similarity	NPC469593
0.8415	Intermediate Similarity	NPC76518
0.8415	Intermediate Similarity	NPC292553
0.8395	Intermediate Similarity	NPC475789
0.8395	Intermediate Similarity	NPC470929
0.8395	Intermediate Similarity	NPC85095
0.8395	Intermediate Similarity	NPC216420
0.8395	Intermediate Similarity	NPC470558
0.8395	Intermediate Similarity	NPC232023
0.8395	Intermediate Similarity	NPC207013
0.8395	Intermediate Similarity	NPC211135
0.8378	Intermediate Similarity	NPC299948
0.8378	Intermediate Similarity	NPC9942
0.8378	Intermediate Similarity	NPC470830
0.8378	Intermediate Similarity	NPC210323
0.8378	Intermediate Similarity	NPC241085
0.8375	Intermediate Similarity	NPC264245
0.8356	Intermediate Similarity	NPC473230
0.8356	Intermediate Similarity	NPC475884
0.8354	Intermediate Similarity	NPC47982
0.8354	Intermediate Similarity	NPC28862
0.8354	Intermediate Similarity	NPC109546
0.8354	Intermediate Similarity	NPC143182
0.8354	Intermediate Similarity	NPC81306
0.8354	Intermediate Similarity	NPC1319
0.8354	Intermediate Similarity	NPC84694
0.8333	Intermediate Similarity	NPC27243
0.8333	Intermediate Similarity	NPC318495
0.8333	Intermediate Similarity	NPC34019
0.8333	Intermediate Similarity	NPC473276
0.8333	Intermediate Similarity	NPC155986
0.8333	Intermediate Similarity	NPC476737
0.8333	Intermediate Similarity	NPC258595
0.8333	Intermediate Similarity	NPC41577
0.8333	Intermediate Similarity	NPC198968
0.8333	Intermediate Similarity	NPC214570
0.8333	Intermediate Similarity	NPC474380
0.8313	Intermediate Similarity	NPC261266
0.8313	Intermediate Similarity	NPC168231
0.8313	Intermediate Similarity	NPC94462
0.8313	Intermediate Similarity	NPC71520
0.8313	Intermediate Similarity	NPC6391
0.8313	Intermediate Similarity	NPC472738
0.8313	Intermediate Similarity	NPC269058
0.8312	Intermediate Similarity	NPC257347
0.8312	Intermediate Similarity	NPC118508
0.8312	Intermediate Similarity	NPC141071
0.8312	Intermediate Similarity	NPC121744
0.8312	Intermediate Similarity	NPC322353
0.8312	Intermediate Similarity	NPC471723
0.8293	Intermediate Similarity	NPC470077
0.8293	Intermediate Similarity	NPC256567
0.8293	Intermediate Similarity	NPC205845
0.8293	Intermediate Similarity	NPC231310
0.8289	Intermediate Similarity	NPC211009
0.8272	Intermediate Similarity	NPC470049
0.8272	Intermediate Similarity	NPC477599
0.8272	Intermediate Similarity	NPC145143
0.8272	Intermediate Similarity	NPC101462
0.8272	Intermediate Similarity	NPC30166
0.8272	Intermediate Similarity	NPC202389
0.8256	Intermediate Similarity	NPC110923
0.8256	Intermediate Similarity	NPC74296
0.8256	Intermediate Similarity	NPC275671
0.825	Intermediate Similarity	NPC236112
0.825	Intermediate Similarity	NPC234193
0.8243	Intermediate Similarity	NPC245795
0.8243	Intermediate Similarity	NPC276616
0.8243	Intermediate Similarity	NPC2648
0.8228	Intermediate Similarity	NPC11908
0.8228	Intermediate Similarity	NPC473943
0.8228	Intermediate Similarity	NPC275910
0.8214	Intermediate Similarity	NPC4643
0.8214	Intermediate Similarity	NPC89747
0.8205	Intermediate Similarity	NPC202642
0.8205	Intermediate Similarity	NPC244488
0.8205	Intermediate Similarity	NPC46160
0.8205	Intermediate Similarity	NPC107059
0.8205	Intermediate Similarity	NPC134330
0.8205	Intermediate Similarity	NPC240604
0.8205	Intermediate Similarity	NPC321381
0.8205	Intermediate Similarity	NPC321016
0.8205	Intermediate Similarity	NPC247325
0.8205	Intermediate Similarity	NPC129165
0.8205	Intermediate Similarity	NPC300324
0.8194	Intermediate Similarity	NPC101128
0.8194	Intermediate Similarity	NPC69149
0.8194	Intermediate Similarity	NPC68656
0.8194	Intermediate Similarity	NPC219940
0.8193	Intermediate Similarity	NPC22133

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 NPC472342 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2474
0.2-0.3	4450
0.3-0.4	1444
0.4-0.5	253
0.5-0.6	158
0.6-0.7	164
0.7-0.8	36
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD7525	Registered
0.8077	Intermediate Similarity	NPD7339	Approved
0.8077	Intermediate Similarity	NPD6942	Approved
0.7976	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6924	Approved
0.7722	Intermediate Similarity	NPD6926	Approved
0.7683	Intermediate Similarity	NPD7645	Phase 2
0.759	Intermediate Similarity	NPD6931	Approved
0.759	Intermediate Similarity	NPD6930	Phase 2
0.7586	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4787	Phase 1
0.7531	Intermediate Similarity	NPD6933	Approved
0.7529	Intermediate Similarity	NPD4788	Approved
0.747	Intermediate Similarity	NPD6929	Approved
0.7468	Intermediate Similarity	NPD4243	Approved
0.7442	Intermediate Similarity	NPD4786	Approved
0.7416	Intermediate Similarity	NPD5328	Approved
0.7381	Intermediate Similarity	NPD4748	Discontinued
0.7326	Intermediate Similarity	NPD6695	Phase 3
0.7294	Intermediate Similarity	NPD6902	Approved
0.7284	Intermediate Similarity	NPD4785	Approved
0.7284	Intermediate Similarity	NPD4784	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7253	Intermediate Similarity	NPD8035	Phase 2
0.7253	Intermediate Similarity	NPD8034	Phase 2
0.7253	Intermediate Similarity	NPD6079	Approved
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7150	Approved
0.725	Intermediate Similarity	NPD7151	Approved
0.725	Intermediate Similarity	NPD7152	Approved
0.7241	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5776	Phase 2
0.7229	Intermediate Similarity	NPD6925	Approved
0.7215	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD6923	Approved
0.7209	Intermediate Similarity	NPD3667	Approved
0.7176	Intermediate Similarity	NPD7514	Phase 3
0.7176	Intermediate Similarity	NPD7509	Discontinued
0.7174	Intermediate Similarity	NPD4202	Approved
0.7159	Intermediate Similarity	NPD6893	Approved
0.7143	Intermediate Similarity	NPD7145	Approved
0.7143	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7144	Approved
0.7125	Intermediate Similarity	NPD7143	Approved
0.7108	Intermediate Similarity	NPD6117	Approved
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7073	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6116	Phase 1
0.7024	Intermediate Similarity	NPD6932	Approved
0.7	Intermediate Similarity	NPD7750	Discontinued
0.7	Intermediate Similarity	NPD7524	Approved
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5275	Approved
0.6988	Remote Similarity	NPD4190	Phase 3
0.6979	Remote Similarity	NPD7638	Approved
0.6977	Remote Similarity	NPD7332	Phase 2
0.6941	Remote Similarity	NPD6118	Approved
0.6941	Remote Similarity	NPD6114	Approved
0.6941	Remote Similarity	NPD6115	Approved
0.6941	Remote Similarity	NPD6697	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD6898	Phase 1
0.6875	Remote Similarity	NPD4755	Approved
0.6875	Remote Similarity	NPD5360	Phase 3
0.6875	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6683	Phase 2
0.686	Remote Similarity	NPD4195	Approved
0.6854	Remote Similarity	NPD3666	Approved
0.6854	Remote Similarity	NPD3665	Phase 1
0.6854	Remote Similarity	NPD3133	Approved
0.68	Remote Similarity	NPD5141	Approved
0.6786	Remote Similarity	NPD3703	Phase 2
0.6786	Remote Similarity	NPD8264	Approved
0.6771	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5285	Approved
0.6735	Remote Similarity	NPD4700	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6707	Remote Similarity	NPD4245	Approved
0.6707	Remote Similarity	NPD4789	Approved
0.6707	Remote Similarity	NPD4244	Approved
0.6702	Remote Similarity	NPD7515	Phase 2
0.6702	Remote Similarity	NPD7087	Discontinued
0.6701	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD6399	Phase 3
0.6629	Remote Similarity	NPD4221	Approved
0.6629	Remote Similarity	NPD4223	Phase 3
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD7632	Discontinued
0.66	Remote Similarity	NPD5224	Approved
0.66	Remote Similarity	NPD4633	Approved
0.6593	Remote Similarity	NPD5329	Approved
0.6591	Remote Similarity	NPD6928	Phase 2
0.6585	Remote Similarity	NPD3698	Phase 2
0.6569	Remote Similarity	NPD5739	Approved
0.6569	Remote Similarity	NPD6402	Approved
0.6569	Remote Similarity	NPD7128	Approved
0.6569	Remote Similarity	NPD6675	Approved
0.6535	Remote Similarity	NPD4754	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6522	Remote Similarity	NPD5279	Phase 3
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4159	Approved
0.6489	Remote Similarity	NPD6051	Approved
0.6484	Remote Similarity	NPD4197	Approved
0.6484	Remote Similarity	NPD3668	Phase 3
0.6465	Remote Similarity	NPD5290	Discontinued
0.6442	Remote Similarity	NPD7320	Approved
0.6442	Remote Similarity	NPD6899	Approved
0.6442	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD4758	Discontinued
0.6422	Remote Similarity	NPD7115	Discovery
0.6408	Remote Similarity	NPD4768	Approved
0.6408	Remote Similarity	NPD4767	Approved
0.6392	Remote Similarity	NPD7748	Approved
0.6381	Remote Similarity	NPD6373	Approved
0.6381	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD6083	Phase 2
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD3671	Phase 1
0.6346	Remote Similarity	NPD5701	Approved
0.6346	Remote Similarity	NPD5697	Approved
0.6344	Remote Similarity	NPD4138	Approved
0.6344	Remote Similarity	NPD4689	Approved
0.6344	Remote Similarity	NPD4690	Approved
0.6344	Remote Similarity	NPD4693	Phase 3
0.6344	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD5205	Approved
0.6344	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD368	Approved
0.6327	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5210	Approved
0.6327	Remote Similarity	NPD4629	Approved
0.6321	Remote Similarity	NPD7290	Approved
0.6321	Remote Similarity	NPD7102	Approved
0.6321	Remote Similarity	NPD6883	Approved
0.6286	Remote Similarity	NPD4730	Approved
0.6286	Remote Similarity	NPD6011	Approved
0.6286	Remote Similarity	NPD5128	Approved
0.6286	Remote Similarity	NPD4729	Approved
0.6265	Remote Similarity	NPD6705	Phase 1
0.6262	Remote Similarity	NPD6617	Approved
0.6262	Remote Similarity	NPD6847	Approved
0.6262	Remote Similarity	NPD8130	Phase 1
0.6262	Remote Similarity	NPD6650	Approved
0.6262	Remote Similarity	NPD6649	Approved
0.6262	Remote Similarity	NPD6869	Approved
0.6262	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6014	Approved
0.6226	Remote Similarity	NPD6013	Approved
0.6226	Remote Similarity	NPD6012	Approved
0.6216	Remote Similarity	NPD7328	Approved
0.6216	Remote Similarity	NPD7327	Approved
0.6211	Remote Similarity	NPD4722	Approved
0.6211	Remote Similarity	NPD4723	Approved
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6882	Approved
0.6204	Remote Similarity	NPD8297	Approved
0.62	Remote Similarity	NPD7902	Approved
0.6186	Remote Similarity	NPD7637	Suspended
0.618	Remote Similarity	NPD3617	Approved
0.618	Remote Similarity	NPD5364	Discontinued
0.617	Remote Similarity	NPD5280	Approved
0.617	Remote Similarity	NPD5690	Phase 2
0.617	Remote Similarity	NPD7334	Approved
0.617	Remote Similarity	NPD5330	Approved
0.617	Remote Similarity	NPD6409	Approved
0.617	Remote Similarity	NPD7146	Approved
0.617	Remote Similarity	NPD4694	Approved
0.617	Remote Similarity	NPD7521	Approved
0.617	Remote Similarity	NPD4519	Discontinued
0.617	Remote Similarity	NPD6684	Approved
0.617	Remote Similarity	NPD4623	Approved
0.6168	Remote Similarity	NPD5250	Approved
0.6168	Remote Similarity	NPD5249	Phase 3
0.6168	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5169	Approved
0.6168	Remote Similarity	NPD5248	Approved
0.6168	Remote Similarity	NPD5135	Approved
0.6168	Remote Similarity	NPD5247	Approved
0.6168	Remote Similarity	NPD5251	Approved
0.6161	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD4139	Approved
0.6154	Remote Similarity	NPD4692	Approved
0.6147	Remote Similarity	NPD8133	Approved
0.6139	Remote Similarity	NPD4225	Approved
0.6132	Remote Similarity	NPD5168	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