NPASS Compound

Structure

NPC272746 OpenBabel07101719252D 32 36 0 0 1 0 0 0 0 0999 V2000 4.7056 0.9418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1028 1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5008 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0143 0.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1321 -2.3483 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 4.0251 -0.9730 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 3.4532 -1.7601 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 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 1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7539 0.7395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4532 -0.1858 0.0000 C 0 0 1 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 0.8426 1.4595 0.0000 C 0 0 2 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 -2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 2 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 1.4595 0.0000 C 0 0 0 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 0.8426 2.4324 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 18 2 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 19 18 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 29 1 6 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 24 27 1 1 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.35
Volume:	494.325
LogP:	5.966
LogD:	5.237
LogS:	-6.175
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	5.052
Fsp3:	0.833
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:	-5.207
MDCK Permeability:	4.468136830837466e-05
Pgp-inhibitor:	0.876
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.889

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.35298919677734%
Volume Distribution (VD):	1.226
Pgp-substrate:	3.009953260421753%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.193
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.295
CYP2C9-substrate:	0.272
CYP2D6-inhibitor:	0.644
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	3.071
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.324
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.882
Carcinogencity:	0.011
Eye Corrosion:	0.783
Eye Irritation:	0.348
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC272746

Natural Product ID:	NPC272746
*Common Name:**	OVNLBUJGQPXGOJ-UNFHKAPWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OVNLBUJGQPXGOJ-UNFHKAPWSA-N
Standard InCHI:	InChI=1S/C30H46O2/c1-18(2)19-9-12-27(5)15-16-29(7)20(24(19)27)17-21(31)25-28(6)13-11-23(32)26(3,4)22(28)10-14-30(25,29)8/h11,13,19-22,24-25,31H,1,9-10,12,14-17H2,2-8H3/t19-,20+,21+,22-,24+,25+,27+,28-,29+,30+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](C[C@H]([C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581945
PubChem CID:	n.a.
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
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT460	Cell Line	MT2	Homo sapiens	CC50	=	60400.0	nM	PMID[545075]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[545075]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	8700.0	nM	PMID[545075]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	6.9	n.a.	PMID[545075]

☑ 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 NPC272746 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	173
0.1-0.2	1161
0.2-0.3	4953
0.3-0.4	13890
0.4-0.5	8750
0.5-0.6	5757
0.6-0.7	4814
0.7-0.8	2729
0.8-0.85	346
0.85-0.9	110
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9651	High Similarity	NPC85173
0.9529	High Similarity	NPC93778
0.9425	High Similarity	NPC126993
0.9302	High Similarity	NPC475740
0.9302	High Similarity	NPC58063
0.9294	High Similarity	NPC470574
0.9205	High Similarity	NPC191684
0.9195	High Similarity	NPC471722
0.9195	High Similarity	NPC328539
0.9186	High Similarity	NPC474733
0.9186	High Similarity	NPC474778
0.9186	High Similarity	NPC31564
0.9186	High Similarity	NPC474732
0.9186	High Similarity	NPC145879
0.9186	High Similarity	NPC72133
0.9176	High Similarity	NPC214043
0.9176	High Similarity	NPC85774
0.9111	High Similarity	NPC471207
0.9101	High Similarity	NPC475806
0.9091	High Similarity	NPC309603
0.9091	High Similarity	NPC275740
0.9091	High Similarity	NPC86319
0.9091	High Similarity	NPC473999
0.9091	High Similarity	NPC119416
0.9091	High Similarity	NPC1015
0.9091	High Similarity	NPC31985
0.908	High Similarity	NPC141292
0.9022	High Similarity	NPC108078
0.9	High Similarity	NPC12722
0.9	High Similarity	NPC475255
0.8989	High Similarity	NPC48010
0.8977	High Similarity	NPC471724
0.8977	High Similarity	NPC474677
0.8977	High Similarity	NPC193360
0.8977	High Similarity	NPC310752
0.8977	High Similarity	NPC206060
0.8977	High Similarity	NPC292491
0.8977	High Similarity	NPC472802
0.8977	High Similarity	NPC143767
0.8977	High Similarity	NPC131470
0.8966	High Similarity	NPC475022
0.8966	High Similarity	NPC118648
0.8966	High Similarity	NPC158393
0.8966	High Similarity	NPC222613
0.8953	High Similarity	NPC473246
0.8953	High Similarity	NPC33913
0.8953	High Similarity	NPC472265
0.8953	High Similarity	NPC221758
0.8953	High Similarity	NPC59453
0.8925	High Similarity	NPC103051
0.8901	High Similarity	NPC245972
0.8901	High Similarity	NPC8993
0.8901	High Similarity	NPC196485
0.8901	High Similarity	NPC111015
0.8889	High Similarity	NPC168027
0.8889	High Similarity	NPC185936
0.8889	High Similarity	NPC473998
0.8876	High Similarity	NPC186688
0.8876	High Similarity	NPC268406
0.8876	High Similarity	NPC26959
0.8864	High Similarity	NPC474684
0.8864	High Similarity	NPC142361
0.8851	High Similarity	NPC469948
0.8851	High Similarity	NPC22133
0.8851	High Similarity	NPC133954
0.8851	High Similarity	NPC76518
0.8837	High Similarity	NPC472743
0.8837	High Similarity	NPC475726
0.8804	High Similarity	NPC259286
0.8804	High Similarity	NPC271195
0.8791	High Similarity	NPC134826
0.8791	High Similarity	NPC474736
0.8791	High Similarity	NPC69454
0.8778	High Similarity	NPC183283
0.8764	High Similarity	NPC474925
0.8764	High Similarity	NPC472739
0.875	High Similarity	NPC269396
0.875	High Similarity	NPC94755
0.875	High Similarity	NPC98236
0.875	High Similarity	NPC51014
0.875	High Similarity	NPC475862
0.875	High Similarity	NPC213412
0.875	High Similarity	NPC74363
0.875	High Similarity	NPC471737
0.8736	High Similarity	NPC329043
0.8736	High Similarity	NPC161423
0.8736	High Similarity	NPC82902
0.8736	High Similarity	NPC227064
0.8736	High Similarity	NPC58841
0.8736	High Similarity	NPC237712
0.8736	High Similarity	NPC474482
0.8736	High Similarity	NPC475745
0.8736	High Similarity	NPC321187
0.8723	High Similarity	NPC114274
0.8721	High Similarity	NPC151519
0.871	High Similarity	NPC473158
0.871	High Similarity	NPC249954
0.8706	High Similarity	NPC472478
0.8696	High Similarity	NPC209662
0.8696	High Similarity	NPC23170
0.8696	High Similarity	NPC299100
0.8681	High Similarity	NPC131872
0.8681	High Similarity	NPC233455
0.8681	High Similarity	NPC233116
0.8681	High Similarity	NPC63748
0.8681	High Similarity	NPC158030
0.8681	High Similarity	NPC65120
0.8681	High Similarity	NPC4036
0.8681	High Similarity	NPC145067
0.8667	High Similarity	NPC477943
0.8667	High Similarity	NPC475921
0.8667	High Similarity	NPC474704
0.8667	High Similarity	NPC474245
0.8667	High Similarity	NPC32830
0.8652	High Similarity	NPC89747
0.8652	High Similarity	NPC187376
0.8652	High Similarity	NPC159046
0.8652	High Similarity	NPC233836
0.8652	High Similarity	NPC136548
0.8652	High Similarity	NPC73064
0.8636	High Similarity	NPC29447
0.8636	High Similarity	NPC474218
0.8636	High Similarity	NPC292553
0.8636	High Similarity	NPC197823
0.8636	High Similarity	NPC471224
0.8632	High Similarity	NPC144956
0.8621	High Similarity	NPC471036
0.8621	High Similarity	NPC291320
0.8617	High Similarity	NPC190554
0.8605	High Similarity	NPC473217
0.8602	High Similarity	NPC180950
0.8587	High Similarity	NPC295643
0.8587	High Similarity	NPC272075
0.8587	High Similarity	NPC474807
0.8587	High Similarity	NPC214756
0.8587	High Similarity	NPC109305
0.8556	High Similarity	NPC53911
0.8556	High Similarity	NPC158778
0.8556	High Similarity	NPC328313
0.8539	High Similarity	NPC55309
0.8539	High Similarity	NPC477579
0.8539	High Similarity	NPC472738
0.8539	High Similarity	NPC235341
0.8539	High Similarity	NPC469994
0.8539	High Similarity	NPC28252
0.8539	High Similarity	NPC95594
0.8539	High Similarity	NPC327115
0.8539	High Similarity	NPC155011
0.8526	High Similarity	NPC194196
0.8523	High Similarity	NPC74595
0.8523	High Similarity	NPC146683
0.8523	High Similarity	NPC474233
0.8523	High Similarity	NPC180834
0.8523	High Similarity	NPC264665
0.8511	High Similarity	NPC301534
0.8511	High Similarity	NPC5532
0.8511	High Similarity	NPC192428
0.8511	High Similarity	NPC250757
0.8511	High Similarity	NPC469545
0.8511	High Similarity	NPC61369
0.8506	High Similarity	NPC48362
0.8495	Intermediate Similarity	NPC474690
0.8495	Intermediate Similarity	NPC166906
0.8488	Intermediate Similarity	NPC2482
0.8488	Intermediate Similarity	NPC476809
0.8478	Intermediate Similarity	NPC212301
0.8478	Intermediate Similarity	NPC86266
0.8478	Intermediate Similarity	NPC155304
0.8478	Intermediate Similarity	NPC110657
0.8478	Intermediate Similarity	NPC189520
0.8471	Intermediate Similarity	NPC82635
0.8462	Intermediate Similarity	NPC128496
0.8462	Intermediate Similarity	NPC76879
0.8462	Intermediate Similarity	NPC472240
0.8462	Intermediate Similarity	NPC69627
0.8462	Intermediate Similarity	NPC472973
0.8462	Intermediate Similarity	NPC102414
0.8462	Intermediate Similarity	NPC2983
0.8462	Intermediate Similarity	NPC84271
0.8462	Intermediate Similarity	NPC122116
0.8462	Intermediate Similarity	NPC77168
0.8462	Intermediate Similarity	NPC262858
0.8444	Intermediate Similarity	NPC90652
0.8444	Intermediate Similarity	NPC102683
0.8444	Intermediate Similarity	NPC98442
0.8444	Intermediate Similarity	NPC130577
0.8444	Intermediate Similarity	NPC57469
0.8444	Intermediate Similarity	NPC293564
0.8444	Intermediate Similarity	NPC475772
0.8444	Intermediate Similarity	NPC242468
0.8444	Intermediate Similarity	NPC4643
0.8444	Intermediate Similarity	NPC171203
0.8444	Intermediate Similarity	NPC317590
0.8444	Intermediate Similarity	NPC68160
0.8444	Intermediate Similarity	NPC142415
0.8444	Intermediate Similarity	NPC307426
0.8444	Intermediate Similarity	NPC88716
0.8444	Intermediate Similarity	NPC51700
0.8444	Intermediate Similarity	NPC18064
0.8438	Intermediate Similarity	NPC154072

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 NPC272746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1420
0.2-0.3	4029
0.3-0.4	2468
0.4-0.5	591
0.5-0.6	168
0.6-0.7	112
0.7-0.8	159
0.8-0.85	33
0.85-0.9	13
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.954	High Similarity	NPD6079	Approved
0.931	High Similarity	NPD5328	Approved
0.9186	High Similarity	NPD3618	Phase 1
0.8953	High Similarity	NPD4786	Approved
0.8913	High Similarity	NPD5221	Approved
0.8913	High Similarity	NPD5222	Approved
0.8913	High Similarity	NPD5220	Clinical (unspecified phase)
0.8817	High Similarity	NPD5173	Approved
0.8791	High Similarity	NPD4202	Approved
0.8736	High Similarity	NPD3666	Approved
0.8736	High Similarity	NPD3665	Phase 1
0.8736	High Similarity	NPD3133	Approved
0.8721	High Similarity	NPD3667	Approved
0.8681	High Similarity	NPD7515	Phase 2
0.8632	High Similarity	NPD5285	Approved
0.8632	High Similarity	NPD5286	Approved
0.8632	High Similarity	NPD4696	Approved
0.8542	High Similarity	NPD5223	Approved
0.8511	High Similarity	NPD4697	Phase 3
0.8454	Intermediate Similarity	NPD5211	Phase 2
0.8454	Intermediate Similarity	NPD5225	Approved
0.8454	Intermediate Similarity	NPD4633	Approved
0.8454	Intermediate Similarity	NPD5224	Approved
0.8454	Intermediate Similarity	NPD5226	Approved
0.8427	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD4755	Approved
0.8367	Intermediate Similarity	NPD5174	Approved
0.8367	Intermediate Similarity	NPD5175	Approved
0.8333	Intermediate Similarity	NPD5279	Phase 3
0.8298	Intermediate Similarity	NPD7748	Approved
0.8295	Intermediate Similarity	NPD4223	Phase 3
0.8295	Intermediate Similarity	NPD4221	Approved
0.8283	Intermediate Similarity	NPD5141	Approved
0.8261	Intermediate Similarity	NPD4753	Phase 2
0.8247	Intermediate Similarity	NPD4700	Approved
0.8222	Intermediate Similarity	NPD5329	Approved
0.8218	Intermediate Similarity	NPD6899	Approved
0.8218	Intermediate Similarity	NPD6881	Approved
0.8211	Intermediate Similarity	NPD4629	Approved
0.8211	Intermediate Similarity	NPD5210	Approved
0.8202	Intermediate Similarity	NPD4788	Approved
0.8152	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD5690	Phase 2
0.8119	Intermediate Similarity	NPD5697	Approved
0.8111	Intermediate Similarity	NPD4197	Approved
0.8068	Intermediate Similarity	NPD7525	Registered
0.8058	Intermediate Similarity	NPD6883	Approved
0.8058	Intermediate Similarity	NPD7290	Approved
0.8058	Intermediate Similarity	NPD7102	Approved
0.8041	Intermediate Similarity	NPD7902	Approved
0.8039	Intermediate Similarity	NPD4730	Approved
0.8039	Intermediate Similarity	NPD5168	Approved
0.8039	Intermediate Similarity	NPD4729	Approved
0.8039	Intermediate Similarity	NPD6011	Approved
0.802	Intermediate Similarity	NPD6675	Approved
0.802	Intermediate Similarity	NPD5739	Approved
0.802	Intermediate Similarity	NPD7128	Approved
0.802	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD4754	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7981	Intermediate Similarity	NPD6649	Approved
0.7981	Intermediate Similarity	NPD6617	Approved
0.7981	Intermediate Similarity	NPD8130	Phase 1
0.7981	Intermediate Similarity	NPD6847	Approved
0.7981	Intermediate Similarity	NPD6650	Approved
0.7981	Intermediate Similarity	NPD6869	Approved
0.7961	Intermediate Similarity	NPD6012	Approved
0.7961	Intermediate Similarity	NPD6014	Approved
0.7961	Intermediate Similarity	NPD6013	Approved
0.7955	Intermediate Similarity	NPD4195	Approved
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7935	Intermediate Similarity	NPD4138	Approved
0.7935	Intermediate Similarity	NPD4689	Approved
0.7935	Intermediate Similarity	NPD4693	Phase 3
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7935	Intermediate Similarity	NPD4690	Approved
0.7935	Intermediate Similarity	NPD5205	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7935	Intermediate Similarity	NPD4688	Approved
0.7912	Intermediate Similarity	NPD3668	Phase 3
0.7907	Intermediate Similarity	NPD7339	Approved
0.7907	Intermediate Similarity	NPD6942	Approved
0.7905	Intermediate Similarity	NPD8297	Approved
0.7905	Intermediate Similarity	NPD6882	Approved
0.7885	Intermediate Similarity	NPD5247	Approved
0.7885	Intermediate Similarity	NPD5135	Approved
0.7885	Intermediate Similarity	NPD5250	Approved
0.7885	Intermediate Similarity	NPD4634	Approved
0.7885	Intermediate Similarity	NPD5169	Approved
0.7885	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5249	Phase 3
0.7885	Intermediate Similarity	NPD5251	Approved
0.7885	Intermediate Similarity	NPD5248	Approved
0.7864	Intermediate Similarity	NPD5128	Approved
0.7864	Intermediate Similarity	NPD7320	Approved
0.7857	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD6084	Phase 2
0.7843	Intermediate Similarity	NPD4767	Approved
0.7843	Intermediate Similarity	NPD4768	Approved
0.7841	Intermediate Similarity	NPD3617	Approved
0.781	Intermediate Similarity	NPD5215	Approved
0.781	Intermediate Similarity	NPD5217	Approved
0.781	Intermediate Similarity	NPD5127	Approved
0.781	Intermediate Similarity	NPD5216	Approved
0.7788	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD6373	Approved
0.7778	Intermediate Similarity	NPD7115	Discovery
0.7778	Intermediate Similarity	NPD7638	Approved
0.7767	Intermediate Similarity	NPD5701	Approved
0.7766	Intermediate Similarity	NPD5737	Approved
0.7766	Intermediate Similarity	NPD6672	Approved
0.7766	Intermediate Similarity	NPD6903	Approved
0.7765	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7645	Phase 2
0.7742	Intermediate Similarity	NPD4694	Approved
0.7742	Intermediate Similarity	NPD5280	Approved
0.7732	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7900	Approved
0.7708	Intermediate Similarity	NPD8034	Phase 2
0.7708	Intermediate Similarity	NPD8035	Phase 2
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7685	Intermediate Similarity	NPD6868	Approved
0.7667	Intermediate Similarity	NPD4695	Discontinued
0.7664	Intermediate Similarity	NPD4632	Approved
0.766	Intermediate Similarity	NPD3573	Approved
0.7647	Intermediate Similarity	NPD4747	Approved
0.7647	Intermediate Similarity	NPD4691	Approved
0.7642	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5290	Discontinued
0.7593	Intermediate Similarity	NPD5167	Approved
0.7586	Intermediate Similarity	NPD4058	Approved
0.7553	Intermediate Similarity	NPD4623	Approved
0.7553	Intermediate Similarity	NPD4519	Discontinued
0.7545	Intermediate Similarity	NPD6335	Approved
0.7529	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4137	Phase 3
0.7529	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5281	Approved
0.7526	Intermediate Similarity	NPD5284	Approved
0.7477	Intermediate Similarity	NPD7101	Approved
0.7477	Intermediate Similarity	NPD7100	Approved
0.7475	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5695	Phase 3
0.7455	Intermediate Similarity	NPD6009	Approved
0.7455	Intermediate Similarity	NPD6317	Approved
0.7429	Intermediate Similarity	NPD6412	Phase 2
0.7426	Intermediate Similarity	NPD5696	Approved
0.7416	Intermediate Similarity	NPD6117	Approved
0.7411	Intermediate Similarity	NPD6054	Approved
0.7387	Intermediate Similarity	NPD6314	Approved
0.7387	Intermediate Similarity	NPD6313	Approved
0.7386	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5733	Approved
0.7386	Intermediate Similarity	NPD4687	Approved
0.7364	Intermediate Similarity	NPD6274	Approved
0.7333	Intermediate Similarity	NPD6116	Phase 1
0.732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6080	Approved
0.732	Intermediate Similarity	NPD6904	Approved
0.732	Intermediate Similarity	NPD6673	Approved
0.7303	Intermediate Similarity	NPD3703	Phase 2
0.7281	Intermediate Similarity	NPD6370	Approved
0.7265	Intermediate Similarity	NPD7736	Approved
0.7257	Intermediate Similarity	NPD6319	Approved
0.7253	Intermediate Similarity	NPD6115	Approved
0.7253	Intermediate Similarity	NPD6118	Approved
0.7253	Intermediate Similarity	NPD6114	Approved
0.7253	Intermediate Similarity	NPD6697	Approved
0.7245	Intermediate Similarity	NPD4096	Approved
0.7241	Intermediate Similarity	NPD4245	Approved
0.7241	Intermediate Similarity	NPD4789	Approved
0.7241	Intermediate Similarity	NPD4244	Approved
0.7217	Intermediate Similarity	NPD7604	Phase 2
0.7216	Intermediate Similarity	NPD5208	Approved
0.7216	Intermediate Similarity	NPD4518	Approved
0.7212	Intermediate Similarity	NPD5091	Approved
0.7209	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5360	Phase 3
0.7204	Intermediate Similarity	NPD4139	Approved
0.7204	Intermediate Similarity	NPD4692	Approved
0.72	Intermediate Similarity	NPD6001	Approved
0.7193	Intermediate Similarity	NPD6015	Approved
0.7193	Intermediate Similarity	NPD5983	Phase 2
0.7193	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6016	Approved
0.7191	Intermediate Similarity	NPD6924	Approved
0.7191	Intermediate Similarity	NPD4784	Approved
0.7191	Intermediate Similarity	NPD4785	Approved
0.7191	Intermediate Similarity	NPD6926	Approved
0.7188	Intermediate Similarity	NPD6098	Approved
0.717	Intermediate Similarity	NPD6008	Approved
0.7159	Intermediate Similarity	NPD7150	Approved
0.7159	Intermediate Similarity	NPD5276	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