NPASS Compound

Structure

NPC99168 OpenBabel07101718242D 32 36 0 0 1 0 0 0 0 0999 V2000 -2.7797 0.5196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2998 2.0518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1861 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6996 0.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 2.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 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 5.6726 0.3561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 1 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	499.598
LogP:	5.82
LogD:	4.759
LogS:	-5.481
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	4.914
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.184
MDCK Permeability:	1.0986810593749397e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.374
Plasma Protein Binding (PPB):	95.53217315673828%
Volume Distribution (VD):	1.092
Pgp-substrate:	1.8981761932373047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.342
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.155
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.705

ADMET: Excretion

Clearance (CL):	5.221
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.47
Carcinogencity:	0.022
Eye Corrosion:	0.143
Eye Irritation:	0.075
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC99168

Natural Product ID:	NPC99168
*Common Name:**	3Beta,29-Dihydroxy-Olean-18-Ene
IUPAC Name:	(3S,4aR,6aS,6aR,6bR,8aS,11R,14aR,14bR)-11-(hydroxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,6,6a,7,8,9,10,13,14,14a-tetradecahydropicen-3-ol
Synonyms:
Standard InCHIKey:	SPDBQPBUXQGJTI-LRFPMJRFSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-25(2)22-10-13-30(7)23(28(22,5)12-11-24(25)32)9-8-20-21-18-26(3,19-31)14-15-27(21,4)16-17-29(20,30)6/h18,20,22-24,31-32H,8-17,19H2,1-7H3/t20-,22+,23-,24+,26-,27-,28+,29-,30-/m1/s1
SMILES:	OC[C@]1(C)CC[C@]2(C(=C1)[C@H]1CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022918
PubChem CID:	60145667
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
NPO33201	celastraceae sp.	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22487595]

☑ 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	2
Others	4

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT460	Cell Line	MT2	Homo sapiens	Activity	=	67.0	%	PMID[523552]
NPT460	Cell Line	MT2	Homo sapiens	CC50	>	100000.0	nM	PMID[523552]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	17.0	%	PMID[523552]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	10380.0	nM	PMID[523552]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	6557.0	nM	PMID[523552]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[523552]

☑ 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 NPC99168 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	206
0.1-0.2	1733
0.2-0.3	7057
0.3-0.4	16582
0.4-0.5	7125
0.5-0.6	4848
0.6-0.7	3636
0.7-0.8	1091
0.8-0.85	269
0.85-0.9	109
0.9-0.95	13
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474989
1.0	High Similarity	NPC470396
1.0	High Similarity	NPC22955
0.9863	High Similarity	NPC291379
0.9863	High Similarity	NPC53744
0.9861	High Similarity	NPC34177
0.9861	High Similarity	NPC157996
0.9861	High Similarity	NPC40394
0.9861	High Similarity	NPC101475
0.9726	High Similarity	NPC196753
0.9726	High Similarity	NPC158662
0.9726	High Similarity	NPC98386
0.9726	High Similarity	NPC253807
0.9726	High Similarity	NPC230295
0.9726	High Similarity	NPC300499
0.9722	High Similarity	NPC290598
0.9722	High Similarity	NPC265328
0.9722	High Similarity	NPC30590
0.9722	High Similarity	NPC120098
0.9722	High Similarity	NPC27765
0.9722	High Similarity	NPC106364
0.9722	High Similarity	NPC122418
0.9583	High Similarity	NPC34700
0.9583	High Similarity	NPC138374
0.9467	High Similarity	NPC295131
0.9444	High Similarity	NPC100334
0.9342	High Similarity	NPC116202
0.9342	High Similarity	NPC242350
0.9324	High Similarity	NPC472805
0.9324	High Similarity	NPC90979
0.9231	High Similarity	NPC238992
0.9221	High Similarity	NPC304285
0.9221	High Similarity	NPC47763
0.92	High Similarity	NPC72507
0.9178	High Similarity	NPC477138
0.9178	High Similarity	NPC243342
0.9103	High Similarity	NPC159168
0.9103	High Similarity	NPC237795
0.9103	High Similarity	NPC82538
0.9103	High Similarity	NPC253402
0.9067	High Similarity	NPC471798
0.9054	High Similarity	NPC66566
0.9054	High Similarity	NPC291503
0.9054	High Similarity	NPC477923
0.9041	High Similarity	NPC211009
0.9041	High Similarity	NPC182717
0.9041	High Similarity	NPC471799
0.9	High Similarity	NPC237344
0.8974	High Similarity	NPC248886
0.8919	High Similarity	NPC471797
0.8919	High Similarity	NPC91858
0.8904	High Similarity	NPC242001
0.8904	High Similarity	NPC167706
0.8904	High Similarity	NPC301226
0.8889	High Similarity	NPC73064
0.8875	High Similarity	NPC133954
0.8875	High Similarity	NPC191965
0.8831	High Similarity	NPC472463
0.8816	High Similarity	NPC470758
0.8816	High Similarity	NPC477924
0.8816	High Similarity	NPC91594
0.8816	High Similarity	NPC470711
0.88	High Similarity	NPC144075
0.878	High Similarity	NPC17733
0.878	High Similarity	NPC473242
0.878	High Similarity	NPC181225
0.878	High Similarity	NPC290690
0.878	High Similarity	NPC470629
0.878	High Similarity	NPC474512
0.8767	High Similarity	NPC145498
0.8767	High Similarity	NPC92801
0.8765	High Similarity	NPC213412
0.8765	High Similarity	NPC95594
0.8765	High Similarity	NPC477579
0.8765	High Similarity	NPC475862
0.8765	High Similarity	NPC84121
0.8765	High Similarity	NPC74363
0.8765	High Similarity	NPC235341
0.8765	High Similarity	NPC137306
0.875	High Similarity	NPC209802
0.875	High Similarity	NPC180834
0.875	High Similarity	NPC208999
0.8701	High Similarity	NPC285761
0.8701	High Similarity	NPC244385
0.8701	High Similarity	NPC6978
0.8701	High Similarity	NPC275910
0.8701	High Similarity	NPC138621
0.8701	High Similarity	NPC167037
0.8684	High Similarity	NPC300324
0.8684	High Similarity	NPC321381
0.8684	High Similarity	NPC240604
0.8684	High Similarity	NPC106432
0.8684	High Similarity	NPC470749
0.8684	High Similarity	NPC477925
0.8684	High Similarity	NPC237460
0.8684	High Similarity	NPC274079
0.8684	High Similarity	NPC189883
0.8684	High Similarity	NPC107059
0.8684	High Similarity	NPC265588
0.8684	High Similarity	NPC321016
0.8675	High Similarity	NPC274330
0.8675	High Similarity	NPC143232
0.8675	High Similarity	NPC198664
0.8675	High Similarity	NPC470588
0.8659	High Similarity	NPC171203
0.8659	High Similarity	NPC102683
0.8659	High Similarity	NPC130577
0.8659	High Similarity	NPC88716
0.8659	High Similarity	NPC18064
0.8659	High Similarity	NPC51700
0.8659	High Similarity	NPC98442
0.8659	High Similarity	NPC142415
0.8659	High Similarity	NPC293564
0.8659	High Similarity	NPC68160
0.8659	High Similarity	NPC307426
0.8659	High Similarity	NPC242468
0.8649	High Similarity	NPC110799
0.8642	High Similarity	NPC477578
0.8608	High Similarity	NPC476646
0.8608	High Similarity	NPC474531
0.859	High Similarity	NPC273410
0.859	High Similarity	NPC80530
0.859	High Similarity	NPC1319
0.8571	High Similarity	NPC214570
0.8571	High Similarity	NPC126369
0.8571	High Similarity	NPC111110
0.8571	High Similarity	NPC155986
0.8571	High Similarity	NPC198968
0.8571	High Similarity	NPC318495
0.8571	High Similarity	NPC130136
0.8571	High Similarity	NPC470589
0.8554	High Similarity	NPC246708
0.8554	High Similarity	NPC52169
0.8554	High Similarity	NPC40552
0.8554	High Similarity	NPC182797
0.8553	High Similarity	NPC141071
0.8553	High Similarity	NPC162742
0.8553	High Similarity	NPC285893
0.8553	High Similarity	NPC230301
0.8553	High Similarity	NPC304309
0.8553	High Similarity	NPC257347
0.8553	High Similarity	NPC212879
0.8553	High Similarity	NPC288035
0.8553	High Similarity	NPC22105
0.8553	High Similarity	NPC104387
0.8553	High Similarity	NPC240235
0.8553	High Similarity	NPC471723
0.8553	High Similarity	NPC231256
0.8553	High Similarity	NPC28657
0.8553	High Similarity	NPC178383
0.8553	High Similarity	NPC136188
0.8553	High Similarity	NPC134847
0.8537	High Similarity	NPC24277
0.8537	High Similarity	NPC72638
0.85	High Similarity	NPC310989
0.8493	Intermediate Similarity	NPC94192
0.8481	Intermediate Similarity	NPC13554
0.8481	Intermediate Similarity	NPC96362
0.8481	Intermediate Similarity	NPC287749
0.8481	Intermediate Similarity	NPC322313
0.8481	Intermediate Similarity	NPC236237
0.8481	Intermediate Similarity	NPC102253
0.8481	Intermediate Similarity	NPC236112
0.8471	Intermediate Similarity	NPC187722
0.8462	Intermediate Similarity	NPC473943
0.8462	Intermediate Similarity	NPC312328
0.8462	Intermediate Similarity	NPC83351
0.8462	Intermediate Similarity	NPC87604
0.8462	Intermediate Similarity	NPC474216
0.8462	Intermediate Similarity	NPC477522
0.8462	Intermediate Similarity	NPC476314
0.8462	Intermediate Similarity	NPC65897
0.8462	Intermediate Similarity	NPC148977
0.8462	Intermediate Similarity	NPC11908
0.8462	Intermediate Similarity	NPC302041
0.8462	Intermediate Similarity	NPC85346
0.8462	Intermediate Similarity	NPC167891
0.8452	Intermediate Similarity	NPC121798
0.8452	Intermediate Similarity	NPC263393
0.8452	Intermediate Similarity	NPC290972
0.8452	Intermediate Similarity	NPC161751
0.8452	Intermediate Similarity	NPC130520
0.8452	Intermediate Similarity	NPC474686
0.8452	Intermediate Similarity	NPC127689
0.8452	Intermediate Similarity	NPC95246
0.8452	Intermediate Similarity	NPC187785
0.8452	Intermediate Similarity	NPC64872
0.8452	Intermediate Similarity	NPC474972
0.8452	Intermediate Similarity	NPC61543
0.8452	Intermediate Similarity	NPC293048
0.8452	Intermediate Similarity	NPC225585
0.8452	Intermediate Similarity	NPC69627
0.8452	Intermediate Similarity	NPC234346
0.8452	Intermediate Similarity	NPC25906
0.8452	Intermediate Similarity	NPC59263
0.8452	Intermediate Similarity	NPC259875
0.8452	Intermediate Similarity	NPC270768
0.8442	Intermediate Similarity	NPC202642
0.8442	Intermediate Similarity	NPC73875
0.8442	Intermediate Similarity	NPC129165

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 NPC99168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1988
0.2-0.3	4189
0.3-0.4	1958
0.4-0.5	453
0.5-0.6	204
0.6-0.7	146
0.7-0.8	17
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9595	High Similarity	NPD7645	Phase 2
0.8553	High Similarity	NPD6942	Approved
0.8553	High Similarity	NPD7339	Approved
0.8481	Intermediate Similarity	NPD7525	Registered
0.8442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7515	Phase 2
0.7865	Intermediate Similarity	NPD7748	Approved
0.7857	Intermediate Similarity	NPD4786	Approved
0.7831	Intermediate Similarity	NPD3667	Approved
0.7722	Intermediate Similarity	NPD6924	Approved
0.7722	Intermediate Similarity	NPD6926	Approved
0.7674	Intermediate Similarity	NPD3618	Phase 1
0.7625	Intermediate Similarity	NPD8264	Approved
0.7614	Intermediate Similarity	NPD5328	Approved
0.7609	Intermediate Similarity	NPD7902	Approved
0.7558	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6933	Approved
0.75	Intermediate Similarity	NPD4785	Approved
0.75	Intermediate Similarity	NPD4784	Approved
0.7468	Intermediate Similarity	NPD7151	Approved
0.7468	Intermediate Similarity	NPD7150	Approved
0.7468	Intermediate Similarity	NPD7152	Approved
0.7468	Intermediate Similarity	NPD4243	Approved
0.7444	Intermediate Similarity	NPD6079	Approved
0.7436	Intermediate Similarity	NPD6923	Approved
0.7436	Intermediate Similarity	NPD6922	Approved
0.7386	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4748	Discontinued
0.7381	Intermediate Similarity	NPD7509	Discontinued
0.7342	Intermediate Similarity	NPD7143	Approved
0.7342	Intermediate Similarity	NPD7144	Approved
0.7283	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7900	Approved
0.7262	Intermediate Similarity	NPD6929	Approved
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3133	Approved
0.7176	Intermediate Similarity	NPD6930	Phase 2
0.7176	Intermediate Similarity	NPD6931	Approved
0.7174	Intermediate Similarity	NPD4202	Approved
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7024	Intermediate Similarity	NPD6932	Approved
0.7024	Intermediate Similarity	NPD5776	Phase 2
0.7024	Intermediate Similarity	NPD6925	Approved
0.6989	Remote Similarity	NPD6399	Phase 3
0.6988	Remote Similarity	NPD5275	Approved
0.6988	Remote Similarity	NPD4190	Phase 3
0.6979	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5221	Approved
0.6947	Remote Similarity	NPD5222	Approved
0.6941	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7145	Approved
0.6932	Remote Similarity	NPD6695	Phase 3
0.6907	Remote Similarity	NPD7640	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.6882	Remote Similarity	NPD8035	Phase 2
0.6882	Remote Similarity	NPD8034	Phase 2
0.6875	Remote Similarity	NPD4755	Approved
0.6875	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD4195	Approved
0.686	Remote Similarity	NPD6683	Phase 2
0.6854	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5290	Discontinued
0.679	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7332	Phase 2
0.6782	Remote Similarity	NPD4695	Discontinued
0.6782	Remote Similarity	NPD7514	Phase 3
0.6778	Remote Similarity	NPD6893	Approved
0.6753	Remote Similarity	NPD368	Approved
0.6739	Remote Similarity	NPD7513	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
0.6705	Remote Similarity	NPD6902	Approved
0.6705	Remote Similarity	NPD6898	Phase 1
0.6703	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5223	Approved
0.663	Remote Similarity	NPD7524	Approved
0.663	Remote Similarity	NPD7750	Discontinued
0.6629	Remote Similarity	NPD4221	Approved
0.6629	Remote Similarity	NPD4223	Phase 3
0.66	Remote Similarity	NPD4633	Approved
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD5211	Phase 2
0.66	Remote Similarity	NPD5224	Approved
0.6593	Remote Similarity	NPD5329	Approved
0.6569	Remote Similarity	NPD5739	Approved
0.6569	Remote Similarity	NPD6675	Approved
0.6569	Remote Similarity	NPD6402	Approved
0.6569	Remote Similarity	NPD7128	Approved
0.6556	Remote Similarity	NPD4788	Approved
0.6535	Remote Similarity	NPD4754	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6526	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6506	Remote Similarity	NPD4787	Phase 1
0.6484	Remote Similarity	NPD4197	Approved
0.6471	Remote Similarity	NPD5141	Approved
0.6465	Remote Similarity	NPD4225	Approved
0.6452	Remote Similarity	NPD3573	Approved
0.6442	Remote Similarity	NPD7320	Approved
0.6442	Remote Similarity	NPD6881	Approved
0.6442	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4768	Approved
0.6408	Remote Similarity	NPD4767	Approved
0.6404	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.64	Remote Similarity	NPD342	Phase 1
0.6386	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6903	Approved
0.6381	Remote Similarity	NPD6373	Approved
0.6381	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD3617	Approved
0.6364	Remote Similarity	NPD6083	Phase 2
0.6354	Remote Similarity	NPD7087	Discontinued
0.6346	Remote Similarity	NPD5697	Approved
0.6346	Remote Similarity	NPD5701	Approved
0.6344	Remote Similarity	NPD4519	Discontinued
0.6344	Remote Similarity	NPD4138	Approved
0.6344	Remote Similarity	NPD4690	Approved
0.6344	Remote Similarity	NPD4623	Approved
0.6344	Remote Similarity	NPD4693	Phase 3
0.6344	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD4689	Approved
0.6344	Remote Similarity	NPD5205	Approved
0.6337	Remote Similarity	NPD4159	Approved
0.6327	Remote Similarity	NPD5210	Approved
0.6327	Remote Similarity	NPD4629	Approved
0.6322	Remote Similarity	NPD6117	Approved
0.6321	Remote Similarity	NPD6883	Approved
0.6321	Remote Similarity	NPD7290	Approved
0.6321	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6051	Approved
0.6286	Remote Similarity	NPD5168	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
0.6279	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7632	Discontinued
0.6273	Remote Similarity	NPD7115	Discovery
0.6273	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7614	Phase 1
0.6262	Remote Similarity	NPD6650	Approved
0.6262	Remote Similarity	NPD6847	Approved
0.6262	Remote Similarity	NPD8130	Phase 1
0.6262	Remote Similarity	NPD6649	Approved
0.6262	Remote Similarity	NPD6869	Approved
0.6262	Remote Similarity	NPD6617	Approved
0.6262	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6116	Phase 1
0.6228	Remote Similarity	NPD8328	Phase 3
0.6226	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6012	Approved
0.6226	Remote Similarity	NPD6013	Approved
0.6226	Remote Similarity	NPD6014	Approved
0.6211	Remote Similarity	NPD4722	Approved
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6211	Remote Similarity	NPD4723	Approved
0.6207	Remote Similarity	NPD3703	Phase 2
0.6204	Remote Similarity	NPD8297	Approved
0.6204	Remote Similarity	NPD6882	Approved
0.6195	Remote Similarity	NPD8033	Approved
0.619	Remote Similarity	NPD6412	Phase 2
0.618	Remote Similarity	NPD6697	Approved
0.618	Remote Similarity	NPD6114	Approved
0.618	Remote Similarity	NPD6118	Approved
0.618	Remote Similarity	NPD6115	Approved
0.617	Remote Similarity	NPD5280	Approved
0.617	Remote Similarity	NPD4694	Approved
0.617	Remote Similarity	NPD5690	Phase 2
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	NPD5248	Approved
0.6168	Remote Similarity	NPD5251	Approved
0.6168	Remote Similarity	NPD5135	Approved
0.6168	Remote Similarity	NPD5169	Approved
0.6168	Remote Similarity	NPD5247	Approved
0.6118	Remote Similarity	NPD4245	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