NPASS Compound

Structure

CID201852 OpenBabel06191715592D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.2783 4.9617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8187 5.8050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3046 3.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8177 2.4335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -2.9572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2494 -2.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5311 0.5232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 4.1195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3581 3.2768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 -1.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6881 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6872 0.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2177 -0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3744 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8433 1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6866 0.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3051 4.9620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8182 4.1192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 2.4338 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6875 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8439 -0.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5317 -1.4606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2180 -1.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6863 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3750 -1.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5314 -0.4864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9737 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 5.0843 -1.9598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3932 -0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 8 30 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 2 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 6 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 24 30 1 6 0 0 0 25 28 1 0 0 0 0 25 29 1 6 0 0 0 26 28 1 0 0 0 0 26 32 1 6 0 0 0 27 31 1 1 0 0 0 27 33 1 0 0 0 0 29 7 1 6 0 0 0 30 31 1 6 0 0 0 31 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.38
Volume:	520.177
LogP:	6.634
LogD:	5.571
LogS:	-5.841
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	5.07
Fsp3:	0.806
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:	-4.885
MDCK Permeability:	1.7233327525900677e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.699

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.306
Plasma Protein Binding (PPB):	95.5322265625%
Volume Distribution (VD):	1.219
Pgp-substrate:	3.0253498554229736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.961
CYP2C9-inhibitor:	0.214
CYP2C9-substrate:	0.372
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.582
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.838

ADMET: Excretion

Clearance (CL):	9.374
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.63
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.795
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.952
Carcinogencity:	0.282
Eye Corrosion:	0.024
Eye Irritation:	0.061
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC201852

Natural Product ID:	NPC201852
*Common Name:**	Suberosol
IUPAC Name:	(3S,5R,10S,13R,14R,15S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,15-diol
Synonyms:	suberosol
Standard InCHIKey:	MJRURUDEESYVHI-UJZFCZBUSA-N
Standard InCHI:	InChI=1S/C31H50O2/c1-19(2)20(3)10-11-21(4)24-18-27(33)31(9)23-12-13-25-28(5,6)26(32)15-16-29(25,7)22(23)14-17-30(24,31)8/h12,14,19,21,24-27,32-33H,3,10-11,13,15-18H2,1-2,4-9H3/t21-,24-,25+,26+,27+,29-,30-,31-/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1C[C@@H]([C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456314
PubChem CID:	21592340
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO4296	Polyalthia suberosa	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8377018]
NPO4296	Polyalthia suberosa	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[8377018]
NPO4296	Polyalthia suberosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4296	Polyalthia suberosa	Species	Annonaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[479868]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3.0	ug.mL-1	PMID[479868]

☑ 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 NPC201852 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	156
0.1-0.2	1239
0.2-0.3	5868
0.3-0.4	16332
0.4-0.5	8606
0.5-0.6	6153
0.6-0.7	3226
0.7-0.8	903
0.8-0.85	157
0.85-0.9	39
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC20853
0.9474	High Similarity	NPC205455
0.9474	High Similarity	NPC186191
0.9474	High Similarity	NPC275910
0.9351	High Similarity	NPC1319
0.9342	High Similarity	NPC214570
0.9268	High Similarity	NPC470542
0.9241	High Similarity	NPC202389
0.9221	High Similarity	NPC477522
0.9221	High Similarity	NPC318136
0.9211	High Similarity	NPC46160
0.9211	High Similarity	NPC202642
0.9211	High Similarity	NPC73875
0.9146	High Similarity	NPC271967
0.9114	High Similarity	NPC6707
0.9079	High Similarity	NPC118508
0.9079	High Similarity	NPC322353
0.9079	High Similarity	NPC121744
0.9036	High Similarity	NPC2158
0.9012	High Similarity	NPC231310
0.9012	High Similarity	NPC124172
0.9012	High Similarity	NPC209802
0.9012	High Similarity	NPC238485
0.8987	High Similarity	NPC26117
0.8974	High Similarity	NPC18603
0.8974	High Similarity	NPC307965
0.8974	High Similarity	NPC76931
0.8961	High Similarity	NPC240604
0.8961	High Similarity	NPC300324
0.8961	High Similarity	NPC96319
0.8961	High Similarity	NPC470362
0.8961	High Similarity	NPC189883
0.8961	High Similarity	NPC321381
0.8961	High Similarity	NPC321016
0.8961	High Similarity	NPC107059
0.8889	High Similarity	NPC470384
0.8875	High Similarity	NPC474531
0.8846	High Similarity	NPC318495
0.8846	High Similarity	NPC155986
0.8846	High Similarity	NPC198968
0.8831	High Similarity	NPC141071
0.8831	High Similarity	NPC471468
0.8831	High Similarity	NPC230301
0.8831	High Similarity	NPC22105
0.8831	High Similarity	NPC136188
0.8831	High Similarity	NPC471723
0.8831	High Similarity	NPC288035
0.8831	High Similarity	NPC285893
0.8831	High Similarity	NPC134847
0.8831	High Similarity	NPC162742
0.8831	High Similarity	NPC257347
0.8831	High Similarity	NPC28657
0.8831	High Similarity	NPC304309
0.8824	High Similarity	NPC107189
0.8816	High Similarity	NPC201373
0.8795	High Similarity	NPC24277
0.8765	High Similarity	NPC87489
0.8765	High Similarity	NPC470614
0.8765	High Similarity	NPC1272
0.875	High Similarity	NPC236112
0.8734	High Similarity	NPC477514
0.8734	High Similarity	NPC87604
0.8734	High Similarity	NPC473943
0.8734	High Similarity	NPC167037
0.8734	High Similarity	NPC285761
0.8734	High Similarity	NPC474216
0.8734	High Similarity	NPC244385
0.8734	High Similarity	NPC6978
0.8734	High Similarity	NPC138621
0.8718	High Similarity	NPC113733
0.8718	High Similarity	NPC237460
0.8718	High Similarity	NPC134330
0.8718	High Similarity	NPC129165
0.869	High Similarity	NPC475772
0.8675	High Similarity	NPC318390
0.8659	High Similarity	NPC477818
0.8659	High Similarity	NPC110778
0.8642	High Similarity	NPC470383
0.8625	High Similarity	NPC143182
0.8625	High Similarity	NPC80530
0.8625	High Similarity	NPC30986
0.8625	High Similarity	NPC84694
0.8625	High Similarity	NPC81306
0.8625	High Similarity	NPC109546
0.8625	High Similarity	NPC328714
0.8625	High Similarity	NPC273410
0.8625	High Similarity	NPC209430
0.8625	High Similarity	NPC28862
0.8625	High Similarity	NPC47982
0.8608	High Similarity	NPC34019
0.8571	High Similarity	NPC474140
0.8554	High Similarity	NPC475798
0.8554	High Similarity	NPC474493
0.8554	High Similarity	NPC127606
0.8537	High Similarity	NPC248886
0.8537	High Similarity	NPC30166
0.8537	High Similarity	NPC101462
0.8537	High Similarity	NPC49964
0.8537	High Similarity	NPC470049
0.8519	High Similarity	NPC234193
0.8519	High Similarity	NPC102253
0.8519	High Similarity	NPC164840
0.8519	High Similarity	NPC236237
0.8519	High Similarity	NPC241290
0.8519	High Similarity	NPC22403
0.8519	High Similarity	NPC209944
0.8519	High Similarity	NPC322313
0.8519	High Similarity	NPC13554
0.85	High Similarity	NPC72507
0.85	High Similarity	NPC302041
0.85	High Similarity	NPC85346
0.85	High Similarity	NPC65897
0.8488	Intermediate Similarity	NPC77168
0.8488	Intermediate Similarity	NPC102414
0.8488	Intermediate Similarity	NPC84271
0.8488	Intermediate Similarity	NPC105495
0.8481	Intermediate Similarity	NPC106432
0.8462	Intermediate Similarity	NPC477138
0.8462	Intermediate Similarity	NPC243342
0.8462	Intermediate Similarity	NPC329090
0.8462	Intermediate Similarity	NPC27395
0.8452	Intermediate Similarity	NPC474349
0.8452	Intermediate Similarity	NPC474189
0.8442	Intermediate Similarity	NPC110799
0.8434	Intermediate Similarity	NPC237795
0.8434	Intermediate Similarity	NPC82538
0.8434	Intermediate Similarity	NPC317458
0.8434	Intermediate Similarity	NPC193870
0.8434	Intermediate Similarity	NPC141941
0.8427	Intermediate Similarity	NPC222845
0.8427	Intermediate Similarity	NPC45324
0.8427	Intermediate Similarity	NPC162001
0.8415	Intermediate Similarity	NPC209620
0.8415	Intermediate Similarity	NPC23852
0.8415	Intermediate Similarity	NPC47761
0.8415	Intermediate Similarity	NPC474759
0.8415	Intermediate Similarity	NPC264245
0.8415	Intermediate Similarity	NPC474683
0.8415	Intermediate Similarity	NPC474752
0.8415	Intermediate Similarity	NPC7505
0.8415	Intermediate Similarity	NPC474731
0.8415	Intermediate Similarity	NPC82986
0.8409	Intermediate Similarity	NPC310013
0.8395	Intermediate Similarity	NPC472463
0.8391	Intermediate Similarity	NPC69622
0.8375	Intermediate Similarity	NPC471798
0.8372	Intermediate Similarity	NPC471722
0.8372	Intermediate Similarity	NPC471952
0.8372	Intermediate Similarity	NPC280556
0.8354	Intermediate Similarity	NPC328104
0.8354	Intermediate Similarity	NPC477923
0.8354	Intermediate Similarity	NPC66566
0.8354	Intermediate Similarity	NPC319090
0.8354	Intermediate Similarity	NPC291503
0.8353	Intermediate Similarity	NPC94462
0.8353	Intermediate Similarity	NPC261266
0.8353	Intermediate Similarity	NPC474970
0.8353	Intermediate Similarity	NPC201273
0.8353	Intermediate Similarity	NPC152808
0.8353	Intermediate Similarity	NPC6391
0.8353	Intermediate Similarity	NPC293287
0.8353	Intermediate Similarity	NPC94755
0.8333	Intermediate Similarity	NPC478102
0.8333	Intermediate Similarity	NPC470077
0.8333	Intermediate Similarity	NPC182717
0.8333	Intermediate Similarity	NPC471799
0.8333	Intermediate Similarity	NPC185568
0.8333	Intermediate Similarity	NPC205845
0.8313	Intermediate Similarity	NPC189972
0.8313	Intermediate Similarity	NPC218616
0.8313	Intermediate Similarity	NPC296701
0.8313	Intermediate Similarity	NPC5985
0.8313	Intermediate Similarity	NPC50964
0.8313	Intermediate Similarity	NPC7988
0.8312	Intermediate Similarity	NPC92801
0.8295	Intermediate Similarity	NPC212948
0.8293	Intermediate Similarity	NPC78545
0.8293	Intermediate Similarity	NPC71535
0.8289	Intermediate Similarity	NPC216460
0.8289	Intermediate Similarity	NPC208999
0.8272	Intermediate Similarity	NPC22955
0.8272	Intermediate Similarity	NPC477819
0.8272	Intermediate Similarity	NPC474989
0.8272	Intermediate Similarity	NPC42853
0.8272	Intermediate Similarity	NPC477817
0.8272	Intermediate Similarity	NPC312328
0.8272	Intermediate Similarity	NPC470396
0.8272	Intermediate Similarity	NPC99168
0.8256	Intermediate Similarity	NPC233836
0.8256	Intermediate Similarity	NPC187376
0.8256	Intermediate Similarity	NPC159046
0.825	Intermediate Similarity	NPC315261
0.825	Intermediate Similarity	NPC265588
0.825	Intermediate Similarity	NPC244488
0.825	Intermediate Similarity	NPC247325
0.8235	Intermediate Similarity	NPC266511
0.8235	Intermediate Similarity	NPC274448
0.8235	Intermediate Similarity	NPC157257
0.8228	Intermediate Similarity	NPC469593
0.8228	Intermediate Similarity	NPC100334

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 NPC201852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1477
0.2-0.3	4334
0.3-0.4	2269
0.4-0.5	503
0.5-0.6	178
0.6-0.7	163
0.7-0.8	60
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8961	High Similarity	NPD3701	Clinical (unspecified phase)
0.8831	High Similarity	NPD7339	Approved
0.8831	High Similarity	NPD6942	Approved
0.8519	High Similarity	NPD4748	Discontinued
0.8519	High Similarity	NPD7525	Registered
0.8462	Intermediate Similarity	NPD6926	Approved
0.8462	Intermediate Similarity	NPD6924	Approved
0.825	Intermediate Similarity	NPD6933	Approved
0.8228	Intermediate Similarity	NPD4785	Approved
0.8228	Intermediate Similarity	NPD4784	Approved
0.8205	Intermediate Similarity	NPD4243	Approved
0.8205	Intermediate Similarity	NPD7151	Approved
0.8205	Intermediate Similarity	NPD7150	Approved
0.8205	Intermediate Similarity	NPD7152	Approved
0.8182	Intermediate Similarity	NPD6923	Approved
0.8182	Intermediate Similarity	NPD6922	Approved
0.8118	Intermediate Similarity	NPD4786	Approved
0.8077	Intermediate Similarity	NPD7144	Approved
0.8077	Intermediate Similarity	NPD7143	Approved
0.8046	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7645	Phase 2
0.7952	Intermediate Similarity	NPD6929	Approved
0.7901	Intermediate Similarity	NPD8264	Approved
0.7882	Intermediate Similarity	NPD3667	Approved
0.7865	Intermediate Similarity	NPD5328	Approved
0.7857	Intermediate Similarity	NPD6931	Approved
0.7857	Intermediate Similarity	NPD7509	Discontinued
0.7857	Intermediate Similarity	NPD6930	Phase 2
0.7802	Intermediate Similarity	NPD4202	Approved
0.7727	Intermediate Similarity	NPD5279	Phase 3
0.7727	Intermediate Similarity	NPD3618	Phase 1
0.7711	Intermediate Similarity	NPD6932	Approved
0.7711	Intermediate Similarity	NPD5776	Phase 2
0.7711	Intermediate Similarity	NPD6925	Approved
0.7701	Intermediate Similarity	NPD3665	Phase 1
0.7701	Intermediate Similarity	NPD3133	Approved
0.7701	Intermediate Similarity	NPD3666	Approved
0.7692	Intermediate Similarity	NPD6079	Approved
0.7683	Intermediate Similarity	NPD4190	Phase 3
0.7683	Intermediate Similarity	NPD5275	Approved
0.7619	Intermediate Similarity	NPD7145	Approved
0.7586	Intermediate Similarity	NPD6695	Phase 3
0.7529	Intermediate Similarity	NPD4195	Approved
0.7529	Intermediate Similarity	NPD6683	Phase 2
0.7528	Intermediate Similarity	NPD4694	Approved
0.7528	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4755	Approved
0.7442	Intermediate Similarity	NPD7514	Phase 3
0.7416	Intermediate Similarity	NPD6893	Approved
0.7412	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6902	Approved
0.732	Intermediate Similarity	NPD4700	Approved
0.732	Intermediate Similarity	NPD5285	Approved
0.732	Intermediate Similarity	NPD5286	Approved
0.732	Intermediate Similarity	NPD4696	Approved
0.7283	Intermediate Similarity	NPD4753	Phase 2
0.7273	Intermediate Similarity	NPD4221	Approved
0.7273	Intermediate Similarity	NPD4223	Phase 3
0.7253	Intermediate Similarity	NPD7750	Discontinued
0.7253	Intermediate Similarity	NPD7524	Approved
0.7245	Intermediate Similarity	NPD5223	Approved
0.7241	Intermediate Similarity	NPD7332	Phase 2
0.7234	Intermediate Similarity	NPD6399	Phase 3
0.7222	Intermediate Similarity	NPD5329	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4697	Phase 3
0.7188	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5221	Approved
0.7188	Intermediate Similarity	NPD5222	Approved
0.7172	Intermediate Similarity	NPD5211	Phase 2
0.7172	Intermediate Similarity	NPD4633	Approved
0.7172	Intermediate Similarity	NPD5226	Approved
0.7172	Intermediate Similarity	NPD5225	Approved
0.7172	Intermediate Similarity	NPD5224	Approved
0.7159	Intermediate Similarity	NPD6898	Phase 1
0.7143	Intermediate Similarity	NPD5690	Phase 2
0.7129	Intermediate Similarity	NPD5739	Approved
0.7129	Intermediate Similarity	NPD6402	Approved
0.7129	Intermediate Similarity	NPD6675	Approved
0.7129	Intermediate Similarity	NPD7128	Approved
0.7128	Intermediate Similarity	NPD5284	Approved
0.7128	Intermediate Similarity	NPD5281	Approved
0.7113	Intermediate Similarity	NPD5173	Approved
0.7111	Intermediate Similarity	NPD3668	Phase 3
0.7111	Intermediate Similarity	NPD4197	Approved
0.71	Intermediate Similarity	NPD5175	Approved
0.71	Intermediate Similarity	NPD5174	Approved
0.71	Intermediate Similarity	NPD4754	Approved
0.7041	Intermediate Similarity	NPD7638	Approved
0.703	Intermediate Similarity	NPD5141	Approved
0.7021	Intermediate Similarity	NPD4096	Approved
0.7	Intermediate Similarity	NPD4788	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6989	Remote Similarity	NPD4518	Approved
0.6988	Remote Similarity	NPD4787	Phase 1
0.697	Remote Similarity	NPD7639	Approved
0.697	Remote Similarity	NPD7640	Approved
0.6966	Remote Similarity	NPD4692	Approved
0.6966	Remote Similarity	NPD4139	Approved
0.6961	Remote Similarity	NPD4768	Approved
0.6961	Remote Similarity	NPD4767	Approved
0.6957	Remote Similarity	NPD4689	Approved
0.6957	Remote Similarity	NPD4690	Approved
0.6957	Remote Similarity	NPD4688	Approved
0.6957	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD7146	Approved
0.6957	Remote Similarity	NPD4693	Phase 3
0.6957	Remote Similarity	NPD7521	Approved
0.6957	Remote Similarity	NPD5330	Approved
0.6957	Remote Similarity	NPD4138	Approved
0.6957	Remote Similarity	NPD6684	Approved
0.6957	Remote Similarity	NPD5205	Approved
0.6957	Remote Similarity	NPD7334	Approved
0.6947	Remote Similarity	NPD7087	Discontinued
0.6947	Remote Similarity	NPD7515	Phase 2
0.6939	Remote Similarity	NPD6084	Phase 2
0.6939	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6915	Remote Similarity	NPD6051	Approved
0.6907	Remote Similarity	NPD5210	Approved
0.6907	Remote Similarity	NPD4629	Approved
0.6907	Remote Similarity	NPD5695	Phase 3
0.6893	Remote Similarity	NPD5701	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6875	Remote Similarity	NPD5133	Approved
0.6869	Remote Similarity	NPD5290	Discontinued
0.6867	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6011	Approved
0.6827	Remote Similarity	NPD5128	Approved
0.6827	Remote Similarity	NPD4729	Approved
0.6827	Remote Similarity	NPD4730	Approved
0.6809	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6903	Approved
0.6809	Remote Similarity	NPD4723	Approved
0.6809	Remote Similarity	NPD4722	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6649	Approved
0.6792	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6050	Approved
0.6771	Remote Similarity	NPD6411	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6744	Remote Similarity	NPD5733	Approved
0.6733	Remote Similarity	NPD4159	Approved
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6698	Remote Similarity	NPD5251	Approved
0.6698	Remote Similarity	NPD5249	Phase 3
0.6698	Remote Similarity	NPD4634	Approved
0.6698	Remote Similarity	NPD5247	Approved
0.6698	Remote Similarity	NPD5250	Approved
0.6698	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5248	Approved
0.6698	Remote Similarity	NPD5135	Approved
0.6698	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6636	Remote Similarity	NPD5216	Approved
0.6636	Remote Similarity	NPD5217	Approved
0.6636	Remote Similarity	NPD5127	Approved
0.6636	Remote Similarity	NPD5215	Approved
0.6633	Remote Similarity	NPD7748	Approved
0.6598	Remote Similarity	NPD5694	Approved
0.6598	Remote Similarity	NPD8034	Phase 2
0.6598	Remote Similarity	NPD7637	Suspended
0.6598	Remote Similarity	NPD8035	Phase 2
0.6596	Remote Similarity	NPD6098	Approved
0.6566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4687	Approved
0.6535	Remote Similarity	NPD5696	Approved
0.6514	Remote Similarity	NPD4632	Approved
0.6512	Remote Similarity	NPD5276	Approved
0.6512	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5168	Approved
0.6495	Remote Similarity	NPD7136	Phase 2
0.6476	Remote Similarity	NPD6008	Approved
0.6458	Remote Similarity	NPD5737	Approved
0.6458	Remote Similarity	NPD6672	Approved
0.6455	Remote Similarity	NPD5167	Approved
0.6444	Remote Similarity	NPD3617	Approved
0.6436	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD6335	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