NPASS Compound

Structure

NPC143133 OpenBabel07101719132D 33 37 0 0 1 0 0 0 0 0999 V2000 -4.7090 -0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5034 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 -0.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1337 2.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0281 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4557 1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7566 -0.7401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4557 0.1860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1051 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 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 3.3729 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4060 -2.3897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1527 -1.2612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 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 22 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 30 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 1 1 6 0 0 0 18 25 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 26 1 0 0 0 0 21 28 1 1 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 6 0 0 0 24 27 1 1 0 0 0 25 32 2 0 0 0 0 25 33 1 0 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:	458.38
Volume:	508.388
LogP:	5.728
LogD:	5.247
LogS:	-4.206
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	4.79
Fsp3:	0.967
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:	-5.339
MDCK Permeability:	8.099936530925333e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.864

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	95.6064224243164%
Volume Distribution (VD):	1.12
Pgp-substrate:	1.9777414798736572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.654
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.777
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	2.462
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.611
Skin Sensitization:	0.349
Carcinogencity:	0.002
Eye Corrosion:	0.745
Eye Irritation:	0.915
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC143133

Natural Product ID:	NPC143133
*Common Name:**	(20R)-3Alpha-Hydroxylupan-29-Oic Acid
IUPAC Name:	(2R)-2-[(1R,3aR,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]propanoic acid
Synonyms:
Standard InCHIKey:	FEHZXRNYETYZHE-QVZPHOOKSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-18(25(32)33)19-10-13-27(4)16-17-29(6)20(24(19)27)8-9-22-28(5)14-12-23(31)26(2,3)21(28)11-15-30(22,29)7/h18-24,31H,8-17H2,1-7H3,(H,32,33)/t18-,19+,20-,21+,22-,23-,24-,27-,28+,29-,30-/m1/s1
SMILES:	C[C@H]([C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109386
PubChem CID:	76321225
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
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[513596]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[513596]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[513596]
NPT27	Others	Unspecified		Activity	=	96.8	%	PMID[513596]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7800.0	nM	PMID[513596]

☑ 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 NPC143133 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	340
0.1-0.2	3151
0.2-0.3	13875
0.3-0.4	10674
0.4-0.5	5630
0.5-0.6	4230
0.6-0.7	3514
0.7-0.8	1048
0.8-0.85	127
0.85-0.9	76
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC298168
0.9718	High Similarity	NPC212733
0.9583	High Similarity	NPC4209
0.9577	High Similarity	NPC167702
0.9577	High Similarity	NPC280026
0.9452	High Similarity	NPC207010
0.9452	High Similarity	NPC317913
0.9444	High Similarity	NPC174964
0.9444	High Similarity	NPC97534
0.9444	High Similarity	NPC195155
0.9342	High Similarity	NPC61107
0.9342	High Similarity	NPC289486
0.9342	High Similarity	NPC30583
0.9333	High Similarity	NPC261616
0.9324	High Similarity	NPC34046
0.9324	High Similarity	NPC80089
0.9324	High Similarity	NPC224802
0.9324	High Similarity	NPC171426
0.9324	High Similarity	NPC324700
0.9315	High Similarity	NPC475742
0.9315	High Similarity	NPC5767
0.92	High Similarity	NPC80891
0.92	High Similarity	NPC201276
0.92	High Similarity	NPC320144
0.9189	High Similarity	NPC221420
0.9189	High Similarity	NPC23884
0.9167	High Similarity	NPC232112
0.9067	High Similarity	NPC185465
0.9028	High Similarity	NPC151018
0.9028	High Similarity	NPC58057
0.9028	High Similarity	NPC320549
0.9028	High Similarity	NPC156277
0.9014	High Similarity	NPC469941
0.9014	High Similarity	NPC252032
0.9014	High Similarity	NPC319671
0.9014	High Similarity	NPC476734
0.8987	High Similarity	NPC264317
0.8987	High Similarity	NPC294438
0.8961	High Similarity	NPC12933
0.8961	High Similarity	NPC58631
0.8919	High Similarity	NPC273366
0.8889	High Similarity	NPC108131
0.8889	High Similarity	NPC477929
0.8875	High Similarity	NPC2783
0.8875	High Similarity	NPC12774
0.8846	High Similarity	NPC121121
0.8831	High Similarity	NPC477851
0.8816	High Similarity	NPC329117
0.8816	High Similarity	NPC472608
0.88	High Similarity	NPC472486
0.88	High Similarity	NPC472487
0.8784	High Similarity	NPC254340
0.8767	High Similarity	NPC89310
0.8765	High Similarity	NPC269360
0.8765	High Similarity	NPC264005
0.8765	High Similarity	NPC33768
0.8765	High Similarity	NPC252714
0.875	High Similarity	NPC131892
0.875	High Similarity	NPC213178
0.875	High Similarity	NPC196197
0.875	High Similarity	NPC327728
0.875	High Similarity	NPC6120
0.8718	High Similarity	NPC48756
0.8718	High Similarity	NPC280781
0.8684	High Similarity	NPC475031
0.8667	High Similarity	NPC125767
0.8667	High Similarity	NPC21220
0.8659	High Similarity	NPC16377
0.8659	High Similarity	NPC471900
0.8659	High Similarity	NPC474719
0.8649	High Similarity	NPC68426
0.8649	High Similarity	NPC477229
0.8649	High Similarity	NPC282905
0.863	High Similarity	NPC477850
0.8625	High Similarity	NPC473336
0.8625	High Similarity	NPC471044
0.8608	High Similarity	NPC268040
0.8592	High Similarity	NPC42060
0.8592	High Similarity	NPC142712
0.8571	High Similarity	NPC243594
0.8571	High Similarity	NPC31031
0.8571	High Similarity	NPC26029
0.8554	High Similarity	NPC57954
0.8554	High Similarity	NPC213832
0.8554	High Similarity	NPC220498
0.8533	High Similarity	NPC159325
0.8533	High Similarity	NPC477930
0.8533	High Similarity	NPC168511
0.8514	High Similarity	NPC469940
0.85	High Similarity	NPC475726
0.85	High Similarity	NPC472743
0.8493	Intermediate Similarity	NPC64466
0.8481	Intermediate Similarity	NPC476071
0.8472	Intermediate Similarity	NPC48079
0.8462	Intermediate Similarity	NPC220379
0.8452	Intermediate Similarity	NPC169933
0.8442	Intermediate Similarity	NPC180199
0.8442	Intermediate Similarity	NPC477919
0.8434	Intermediate Similarity	NPC4309
0.8421	Intermediate Similarity	NPC267753
0.8421	Intermediate Similarity	NPC472311
0.8421	Intermediate Similarity	NPC159789
0.8415	Intermediate Similarity	NPC302111
0.8415	Intermediate Similarity	NPC472272
0.84	Intermediate Similarity	NPC310766
0.84	Intermediate Similarity	NPC81759
0.8395	Intermediate Similarity	NPC475745
0.8395	Intermediate Similarity	NPC74595
0.8395	Intermediate Similarity	NPC319909
0.8395	Intermediate Similarity	NPC473299
0.8395	Intermediate Similarity	NPC264665
0.8395	Intermediate Similarity	NPC474482
0.8395	Intermediate Similarity	NPC474996
0.8356	Intermediate Similarity	NPC472741
0.8356	Intermediate Similarity	NPC473225
0.8353	Intermediate Similarity	NPC475416
0.8333	Intermediate Similarity	NPC476732
0.8333	Intermediate Similarity	NPC271974
0.8333	Intermediate Similarity	NPC268736
0.8333	Intermediate Similarity	NPC477931
0.8333	Intermediate Similarity	NPC247312
0.8333	Intermediate Similarity	NPC199965
0.8312	Intermediate Similarity	NPC477933
0.8312	Intermediate Similarity	NPC108840
0.8312	Intermediate Similarity	NPC477932
0.8293	Intermediate Similarity	NPC292553
0.8293	Intermediate Similarity	NPC62572
0.8289	Intermediate Similarity	NPC130011
0.8289	Intermediate Similarity	NPC133922
0.8256	Intermediate Similarity	NPC291373
0.8256	Intermediate Similarity	NPC473690
0.8256	Intermediate Similarity	NPC244356
0.8256	Intermediate Similarity	NPC471902
0.8256	Intermediate Similarity	NPC287118
0.8256	Intermediate Similarity	NPC224060
0.825	Intermediate Similarity	NPC469745
0.825	Intermediate Similarity	NPC474870
0.825	Intermediate Similarity	NPC73515
0.825	Intermediate Similarity	NPC271572
0.8243	Intermediate Similarity	NPC474962
0.8243	Intermediate Similarity	NPC321732
0.8243	Intermediate Similarity	NPC324607
0.8243	Intermediate Similarity	NPC129829
0.8243	Intermediate Similarity	NPC254037
0.8235	Intermediate Similarity	NPC77756
0.8219	Intermediate Similarity	NPC478180
0.8219	Intermediate Similarity	NPC41542
0.8219	Intermediate Similarity	NPC130459
0.8219	Intermediate Similarity	NPC474221
0.8214	Intermediate Similarity	NPC146937
0.8205	Intermediate Similarity	NPC474404
0.8205	Intermediate Similarity	NPC477918
0.8194	Intermediate Similarity	NPC230047
0.8194	Intermediate Similarity	NPC19311
0.8193	Intermediate Similarity	NPC98236
0.8193	Intermediate Similarity	NPC269396
0.8193	Intermediate Similarity	NPC472738
0.8182	Intermediate Similarity	NPC477934
0.8171	Intermediate Similarity	NPC219535
0.8171	Intermediate Similarity	NPC237938
0.8171	Intermediate Similarity	NPC474233
0.8171	Intermediate Similarity	NPC475509
0.8169	Intermediate Similarity	NPC114891
0.8161	Intermediate Similarity	NPC303863
0.8161	Intermediate Similarity	NPC277399
0.814	Intermediate Similarity	NPC160506
0.814	Intermediate Similarity	NPC471901
0.8133	Intermediate Similarity	NPC231945
0.8133	Intermediate Similarity	NPC192192
0.8125	Intermediate Similarity	NPC470609
0.8118	Intermediate Similarity	NPC24705
0.8118	Intermediate Similarity	NPC56962
0.8108	Intermediate Similarity	NPC103647
0.8108	Intermediate Similarity	NPC31187
0.8108	Intermediate Similarity	NPC2568
0.8108	Intermediate Similarity	NPC281203
0.8108	Intermediate Similarity	NPC100917
0.8108	Intermediate Similarity	NPC469724
0.8108	Intermediate Similarity	NPC260319
0.8108	Intermediate Similarity	NPC180777
0.8095	Intermediate Similarity	NPC57469
0.8095	Intermediate Similarity	NPC4643
0.8095	Intermediate Similarity	NPC142361
0.8095	Intermediate Similarity	NPC474684
0.8077	Intermediate Similarity	NPC471046
0.8072	Intermediate Similarity	NPC131350
0.8072	Intermediate Similarity	NPC201655
0.8072	Intermediate Similarity	NPC98270
0.8052	Intermediate Similarity	NPC472854
0.8049	Intermediate Similarity	NPC245866
0.8049	Intermediate Similarity	NPC5280
0.8049	Intermediate Similarity	NPC471037
0.8049	Intermediate Similarity	NPC327451
0.8028	Intermediate Similarity	NPC71460
0.8028	Intermediate Similarity	NPC148174
0.8028	Intermediate Similarity	NPC218585
0.8026	Intermediate Similarity	NPC473267
0.8026	Intermediate Similarity	NPC127094
0.8025	Intermediate Similarity	NPC50658
0.8	Intermediate Similarity	NPC192744

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 NPC143133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	3408
0.2-0.3	3670
0.3-0.4	1042
0.4-0.5	267
0.5-0.6	217
0.6-0.7	131
0.7-0.8	15
0.8-0.85	11
0.85-0.9	4
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD6117	Approved
0.9577	High Similarity	NPD6113	Clinical (unspecified phase)
0.9452	High Similarity	NPD6116	Phase 1
0.9324	High Similarity	NPD6697	Approved
0.9324	High Similarity	NPD6118	Approved
0.9324	High Similarity	NPD6115	Approved
0.9324	High Similarity	NPD6114	Approved
0.9028	High Similarity	NPD4809	Clinical (unspecified phase)
0.9028	High Similarity	NPD4808	Clinical (unspecified phase)
0.8987	High Similarity	NPD7520	Clinical (unspecified phase)
0.875	High Similarity	NPD3699	Clinical (unspecified phase)
0.875	High Similarity	NPD3700	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD3703	Phase 2
0.8378	Intermediate Similarity	NPD4244	Approved
0.8378	Intermediate Similarity	NPD4245	Approved
0.8378	Intermediate Similarity	NPD4789	Approved
0.8356	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD5360	Phase 3
0.8333	Intermediate Similarity	NPD4224	Phase 2
0.8267	Intermediate Similarity	NPD6081	Approved
0.8243	Intermediate Similarity	NPD3698	Phase 2
0.8194	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD8034	Phase 2
0.814	Intermediate Similarity	NPD8035	Phase 2
0.8026	Intermediate Similarity	NPD5777	Approved
0.7949	Intermediate Similarity	NPD3702	Approved
0.7875	Intermediate Similarity	NPD3671	Phase 1
0.7792	Intermediate Similarity	NPD4758	Discontinued
0.7763	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7515	Phase 2
0.7439	Intermediate Similarity	NPD5364	Discontinued
0.7436	Intermediate Similarity	NPD4787	Phase 1
0.734	Intermediate Similarity	NPD8418	Phase 2
0.7326	Intermediate Similarity	NPD4786	Approved
0.7303	Intermediate Similarity	NPD5328	Approved
0.726	Intermediate Similarity	NPD3198	Approved
0.7209	Intermediate Similarity	NPD4788	Approved
0.7174	Intermediate Similarity	NPD7748	Approved
0.7159	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6079	Approved
0.7093	Intermediate Similarity	NPD3667	Approved
0.7065	Intermediate Similarity	NPD6399	Phase 3
0.7059	Intermediate Similarity	NPD6928	Phase 2
0.6947	Remote Similarity	NPD7902	Approved
0.6882	Remote Similarity	NPD4202	Approved
0.6875	Remote Similarity	NPD7638	Approved
0.686	Remote Similarity	NPD7525	Registered
0.6813	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD7639	Approved
0.68	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6675	Approved
0.68	Remote Similarity	NPD6402	Approved
0.6742	Remote Similarity	NPD3665	Phase 1
0.6742	Remote Similarity	NPD3133	Approved
0.6742	Remote Similarity	NPD3666	Approved
0.67	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6632	Remote Similarity	NPD7900	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6372	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.6598	Remote Similarity	NPD6083	Phase 2
0.6598	Remote Similarity	NPD5173	Approved
0.6598	Remote Similarity	NPD6084	Phase 2
0.6598	Remote Similarity	NPD4755	Approved
0.6593	Remote Similarity	NPD7334	Approved
0.6593	Remote Similarity	NPD6409	Approved
0.6593	Remote Similarity	NPD5330	Approved
0.6593	Remote Similarity	NPD7146	Approved
0.6593	Remote Similarity	NPD6684	Approved
0.6593	Remote Similarity	NPD7521	Approved
0.6569	Remote Similarity	NPD5701	Approved
0.6569	Remote Similarity	NPD5697	Approved
0.6552	Remote Similarity	NPD7645	Phase 2
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6509	Remote Similarity	NPD8298	Phase 2
0.6505	Remote Similarity	NPD6011	Approved
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD6617	Approved
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8130	Phase 1
0.6471	Remote Similarity	NPD6920	Discontinued
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6465	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD4700	Approved
0.6465	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD5286	Approved
0.6452	Remote Similarity	NPD6672	Approved
0.6452	Remote Similarity	NPD6903	Approved
0.6452	Remote Similarity	NPD5737	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD3617	Approved
0.6415	Remote Similarity	NPD8297	Approved
0.6415	Remote Similarity	NPD6882	Approved
0.6413	Remote Similarity	NPD5279	Phase 3
0.64	Remote Similarity	NPD5223	Approved
0.6389	Remote Similarity	NPD6940	Discontinued
0.6383	Remote Similarity	NPD4753	Phase 2
0.6374	Remote Similarity	NPD3668	Phase 3
0.6355	Remote Similarity	NPD8133	Approved
0.6351	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6415	Discontinued
0.6341	Remote Similarity	NPD6705	Phase 1
0.6337	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD5211	Phase 2
0.6337	Remote Similarity	NPD4633	Approved
0.6337	Remote Similarity	NPD5225	Approved
0.6333	Remote Similarity	NPD4221	Approved
0.6333	Remote Similarity	NPD4223	Phase 3
0.633	Remote Similarity	NPD7115	Discovery
0.6304	Remote Similarity	NPD5329	Approved
0.6275	Remote Similarity	NPD4754	Approved
0.6275	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5175	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7909	Approved
0.6239	Remote Similarity	NPD6868	Approved
0.6237	Remote Similarity	NPD6098	Approved
0.6237	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5695	Phase 3
0.6222	Remote Similarity	NPD4692	Approved
0.6222	Remote Similarity	NPD4139	Approved
0.6214	Remote Similarity	NPD5141	Approved
0.6211	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD5696	Approved
0.6196	Remote Similarity	NPD4197	Approved
0.6186	Remote Similarity	NPD8171	Discontinued
0.6154	Remote Similarity	NPD4767	Approved
0.6154	Remote Similarity	NPD4768	Approved
0.6146	Remote Similarity	NPD6700	Approved
0.6146	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6335	Approved
0.6111	Remote Similarity	NPD4748	Discontinued
0.6091	Remote Similarity	NPD6274	Approved
0.6082	Remote Similarity	NPD6702	Approved
0.6082	Remote Similarity	NPD5284	Approved
0.6082	Remote Similarity	NPD5281	Approved
0.6082	Remote Similarity	NPD6703	Approved
0.6078	Remote Similarity	NPD1700	Approved
0.6071	Remote Similarity	NPD7101	Approved
0.6071	Remote Similarity	NPD7100	Approved
0.6067	Remote Similarity	NPD4802	Phase 2
0.6067	Remote Similarity	NPD4238	Approved
0.6064	Remote Similarity	NPD4690	Approved
0.6064	Remote Similarity	NPD4688	Approved
0.6064	Remote Similarity	NPD4138	Approved
0.6064	Remote Similarity	NPD4689	Approved
0.6064	Remote Similarity	NPD5205	Approved
0.6064	Remote Similarity	NPD4693	Phase 3
0.6061	Remote Similarity	NPD4629	Approved
0.6061	Remote Similarity	NPD5210	Approved
0.6056	Remote Similarity	NPD384	Approved
0.6056	Remote Similarity	NPD385	Approved
0.6042	Remote Similarity	NPD6673	Approved
0.6042	Remote Similarity	NPD6080	Approved
0.6042	Remote Similarity	NPD6904	Approved
0.6038	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4729	Approved
0.6038	Remote Similarity	NPD5128	Approved
0.6038	Remote Similarity	NPD4730	Approved
0.6038	Remote Similarity	NPD5168	Approved
0.6036	Remote Similarity	NPD6009	Approved
0.6036	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6317	Approved
0.6034	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD3573	Approved
0.5982	Remote Similarity	NPD6314	Approved
0.5982	Remote Similarity	NPD6313	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6926	Approved
0.5977	Remote Similarity	NPD6924	Approved
0.5965	Remote Similarity	NPD6908	Approved
0.5965	Remote Similarity	NPD6909	Approved
0.596	Remote Similarity	NPD6001	Approved
0.5943	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6412	Phase 2

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