NPASS Compound

Structure

NPC5767 OpenBabel07101719522D 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 3.5008 -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 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 -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 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 -3.4532 1.7601 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 1.9459 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 -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 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 2 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 2.5279 -1.4595 0.0000 C 0 0 0 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 -2.5279 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1645 2.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1028 -1.4626 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 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 22 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 29 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 30 1 0 0 0 0 18 31 2 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 27 1 6 0 0 0 21 25 1 0 0 0 0 21 26 1 1 0 0 0 22 26 1 1 0 0 0 22 28 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 29 1 1 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 1 0 0 0 29 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.36
Volume:	491.092
LogP:	4.617
LogD:	4.683
LogS:	-4.6
# 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:	0.548
Synthetic Accessibility Score:	4.745
Fsp3:	0.966
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:	-5.174
MDCK Permeability:	2.9802042263327166e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	95.87083435058594%
Volume Distribution (VD):	1.295
Pgp-substrate:	1.6139099597930908%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.457
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.456
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.525
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	4.802
Half-life (T1/2):	0.285

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.811
Skin Sensitization:	0.481
Carcinogencity:	0.005
Eye Corrosion:	0.84
Eye Irritation:	0.723
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC5767

Natural Product ID:	NPC5767
*Common Name:**	Rel-3Alpha,28-Dihydroxy-30-Norlupan-20-One
IUPAC Name:	1-[(1R,3aS,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bS)-9-hydroxy-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]ethanone
Synonyms:
Standard InCHIKey:	BSALBDFYJLSIOZ-AJVVGMEXSA-N
Standard InCHI:	InChI=1S/C29H48O3/c1-18(31)19-9-14-29(17-30)16-15-27(5)20(24(19)29)7-8-22-26(4)12-11-23(32)25(2,3)21(26)10-13-28(22,27)6/h19-24,30,32H,7-17H2,1-6H3/t19-,20+,21-,22+,23+,24+,26-,27+,28+,29+/m0/s1
SMILES:	OC[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@H](C3(C)C)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109395
PubChem CID:	76317491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0004159] 18-hydroxysteroids

*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

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4

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[533700]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[533700]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[533700]

☑ 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 NPC5767 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	338
0.1-0.2	3312
0.2-0.3	13815
0.3-0.4	11356
0.4-0.5	5303
0.5-0.6	4620
0.6-0.7	2854
0.7-0.8	885
0.8-0.85	134
0.85-0.9	53
0.9-0.95	20
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475742
0.9859	High Similarity	NPC221420
0.9857	High Similarity	NPC195155
0.9857	High Similarity	NPC174964
0.9857	High Similarity	NPC97534
0.9583	High Similarity	NPC23884
0.9571	High Similarity	NPC232112
0.9444	High Similarity	NPC472486
0.9444	High Similarity	NPC472487
0.9429	High Similarity	NPC320549
0.9429	High Similarity	NPC156277
0.9429	High Similarity	NPC151018
0.9429	High Similarity	NPC58057
0.9315	High Similarity	NPC298168
0.9315	High Similarity	NPC143133
0.9306	High Similarity	NPC21220
0.9306	High Similarity	NPC273366
0.9306	High Similarity	NPC125767
0.9211	High Similarity	NPC61107
0.9211	High Similarity	NPC289486
0.9211	High Similarity	NPC30583
0.9167	High Similarity	NPC254340
0.9155	High Similarity	NPC89310
0.9143	High Similarity	NPC327728
0.9143	High Similarity	NPC213178
0.9143	High Similarity	NPC131892
0.9143	High Similarity	NPC6120
0.9067	High Similarity	NPC320144
0.9054	High Similarity	NPC475031
0.9041	High Similarity	NPC212733
0.9041	High Similarity	NPC159789
0.9028	High Similarity	NPC477229
0.9028	High Similarity	NPC68426
0.9028	High Similarity	NPC282905
0.8961	High Similarity	NPC268040
0.8933	High Similarity	NPC185465
0.8919	High Similarity	NPC4209
0.8904	High Similarity	NPC168511
0.8904	High Similarity	NPC133922
0.8904	High Similarity	NPC167702
0.8904	High Similarity	NPC159325
0.8904	High Similarity	NPC280026
0.8846	High Similarity	NPC475726
0.8846	High Similarity	NPC472743
0.88	High Similarity	NPC207010
0.88	High Similarity	NPC317913
0.8784	High Similarity	NPC267753
0.8767	High Similarity	NPC310766
0.8767	High Similarity	NPC81759
0.8734	High Similarity	NPC474996
0.8734	High Similarity	NPC474482
0.8734	High Similarity	NPC475745
0.8732	High Similarity	NPC473225
0.8714	High Similarity	NPC142712
0.8701	High Similarity	NPC261616
0.8684	High Similarity	NPC34046
0.8684	High Similarity	NPC80089
0.8684	High Similarity	NPC224802
0.8684	High Similarity	NPC324700
0.8684	High Similarity	NPC171426
0.8667	High Similarity	NPC108840
0.8649	High Similarity	NPC130011
0.8642	High Similarity	NPC4643
0.8642	High Similarity	NPC57469
0.8625	High Similarity	NPC292553
0.8611	High Similarity	NPC324607
0.8611	High Similarity	NPC321732
0.8608	High Similarity	NPC327451
0.8592	High Similarity	NPC48079
0.8592	High Similarity	NPC472984
0.859	High Similarity	NPC469745
0.8571	High Similarity	NPC201276
0.8571	High Similarity	NPC80891
0.8519	High Similarity	NPC472738
0.85	High Similarity	NPC74595
0.85	High Similarity	NPC50438
0.85	High Similarity	NPC264665
0.85	High Similarity	NPC474233
0.8493	Intermediate Similarity	NPC108131
0.8481	Intermediate Similarity	NPC317066
0.8472	Intermediate Similarity	NPC260319
0.8472	Intermediate Similarity	NPC472741
0.8472	Intermediate Similarity	NPC180777
0.8472	Intermediate Similarity	NPC103647
0.8472	Intermediate Similarity	NPC2568
0.8462	Intermediate Similarity	NPC470609
0.8462	Intermediate Similarity	NPC477851
0.84	Intermediate Similarity	NPC472854
0.8395	Intermediate Similarity	NPC294438
0.8395	Intermediate Similarity	NPC264317
0.8378	Intermediate Similarity	NPC473267
0.8356	Intermediate Similarity	NPC252032
0.8356	Intermediate Similarity	NPC476734
0.8356	Intermediate Similarity	NPC469941
0.8356	Intermediate Similarity	NPC129829
0.8356	Intermediate Similarity	NPC254037
0.8356	Intermediate Similarity	NPC319671
0.8354	Intermediate Similarity	NPC12933
0.8354	Intermediate Similarity	NPC50658
0.8354	Intermediate Similarity	NPC58631
0.8333	Intermediate Similarity	NPC201459
0.8313	Intermediate Similarity	NPC472739
0.8313	Intermediate Similarity	NPC474719
0.8312	Intermediate Similarity	NPC264602
0.8293	Intermediate Similarity	NPC12774
0.8293	Intermediate Similarity	NPC476727
0.8293	Intermediate Similarity	NPC80700
0.8293	Intermediate Similarity	NPC98236
0.8293	Intermediate Similarity	NPC269396
0.8293	Intermediate Similarity	NPC476726
0.8293	Intermediate Similarity	NPC2783
0.8289	Intermediate Similarity	NPC472311
0.8286	Intermediate Similarity	NPC114891
0.8272	Intermediate Similarity	NPC473336
0.8272	Intermediate Similarity	NPC105895
0.8272	Intermediate Similarity	NPC471044
0.825	Intermediate Similarity	NPC328007
0.825	Intermediate Similarity	NPC121121
0.8243	Intermediate Similarity	NPC477929
0.8243	Intermediate Similarity	NPC231945
0.8243	Intermediate Similarity	NPC192192
0.8243	Intermediate Similarity	NPC476731
0.8228	Intermediate Similarity	NPC164999
0.8219	Intermediate Similarity	NPC474954
0.8214	Intermediate Similarity	NPC122116
0.8205	Intermediate Similarity	NPC26029
0.8205	Intermediate Similarity	NPC472608
0.8205	Intermediate Similarity	NPC329117
0.8193	Intermediate Similarity	NPC263802
0.8193	Intermediate Similarity	NPC33768
0.8193	Intermediate Similarity	NPC269360
0.8193	Intermediate Similarity	NPC264005
0.8193	Intermediate Similarity	NPC252714
0.8171	Intermediate Similarity	NPC76518
0.8171	Intermediate Similarity	NPC62572
0.8143	Intermediate Similarity	NPC148174
0.8143	Intermediate Similarity	NPC71460
0.8143	Intermediate Similarity	NPC218585
0.814	Intermediate Similarity	NPC224060
0.814	Intermediate Similarity	NPC244356
0.8133	Intermediate Similarity	NPC290058
0.8133	Intermediate Similarity	NPC247195
0.8133	Intermediate Similarity	NPC126642
0.8133	Intermediate Similarity	NPC127094
0.8125	Intermediate Similarity	NPC280781
0.8125	Intermediate Similarity	NPC48756
0.8125	Intermediate Similarity	NPC474484
0.8125	Intermediate Similarity	NPC476071
0.8125	Intermediate Similarity	NPC103754
0.8108	Intermediate Similarity	NPC196197
0.8095	Intermediate Similarity	NPC16377
0.8095	Intermediate Similarity	NPC471900
0.8082	Intermediate Similarity	NPC473230
0.8082	Intermediate Similarity	NPC475884
0.8077	Intermediate Similarity	NPC472746
0.8072	Intermediate Similarity	NPC472272
0.8072	Intermediate Similarity	NPC302111
0.8072	Intermediate Similarity	NPC471737
0.8056	Intermediate Similarity	NPC473276
0.8056	Intermediate Similarity	NPC41577
0.8056	Intermediate Similarity	NPC474380
0.8052	Intermediate Similarity	NPC27349
0.8052	Intermediate Similarity	NPC24014
0.8052	Intermediate Similarity	NPC72444
0.8049	Intermediate Similarity	NPC319909
0.8049	Intermediate Similarity	NPC237938
0.8049	Intermediate Similarity	NPC34984
0.8049	Intermediate Similarity	NPC219535
0.8049	Intermediate Similarity	NPC146683
0.8049	Intermediate Similarity	NPC25037
0.8	Intermediate Similarity	NPC220498
0.8	Intermediate Similarity	NPC282454
0.8	Intermediate Similarity	NPC477850
0.8	Intermediate Similarity	NPC61688
0.8	Intermediate Similarity	NPC213832
0.8	Intermediate Similarity	NPC57954
0.7976	Intermediate Similarity	NPC202937
0.7975	Intermediate Similarity	NPC478128
0.7975	Intermediate Similarity	NPC31031
0.7975	Intermediate Similarity	NPC243594
0.7973	Intermediate Similarity	NPC475977
0.7949	Intermediate Similarity	NPC471046
0.7945	Intermediate Similarity	NPC42060
0.7945	Intermediate Similarity	NPC44122
0.7927	Intermediate Similarity	NPC163616
0.7927	Intermediate Similarity	NPC118800
0.7927	Intermediate Similarity	NPC175410
0.7927	Intermediate Similarity	NPC471036
0.7927	Intermediate Similarity	NPC472744
0.7927	Intermediate Similarity	NPC291320
0.7922	Intermediate Similarity	NPC477930
0.7922	Intermediate Similarity	NPC477508
0.7917	Intermediate Similarity	NPC69149
0.7917	Intermediate Similarity	NPC281540
0.7917	Intermediate Similarity	NPC118937
0.7917	Intermediate Similarity	NPC159654
0.7917	Intermediate Similarity	NPC167995
0.7907	Intermediate Similarity	NPC169933
0.7907	Intermediate Similarity	NPC476296
0.7907	Intermediate Similarity	NPC77756

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 NPC5767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	3645
0.2-0.3	3618
0.3-0.4	928
0.4-0.5	210
0.5-0.6	198
0.6-0.7	135
0.7-0.8	19
0.8-0.85	3
0.85-0.9	15
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9429	High Similarity	NPD4808	Clinical (unspecified phase)
0.9429	High Similarity	NPD4809	Clinical (unspecified phase)
0.9143	High Similarity	NPD3699	Clinical (unspecified phase)
0.9143	High Similarity	NPD3700	Clinical (unspecified phase)
0.9041	High Similarity	NPD3703	Phase 2
0.8919	High Similarity	NPD6117	Approved
0.8904	High Similarity	NPD6113	Clinical (unspecified phase)
0.88	High Similarity	NPD6116	Phase 1
0.875	High Similarity	NPD4244	Approved
0.875	High Similarity	NPD4789	Approved
0.875	High Similarity	NPD4245	Approved
0.8732	High Similarity	NPD5361	Clinical (unspecified phase)
0.8732	High Similarity	NPD5360	Phase 3
0.8684	High Similarity	NPD6115	Approved
0.8684	High Similarity	NPD6114	Approved
0.8684	High Similarity	NPD6697	Approved
0.8684	High Similarity	NPD6118	Approved
0.8611	High Similarity	NPD3698	Phase 2
0.8571	High Similarity	NPD3171	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3671	Phase 1
0.8133	Intermediate Similarity	NPD4758	Discontinued
0.7945	Intermediate Similarity	NPD4224	Phase 2
0.7895	Intermediate Similarity	NPD6081	Approved
0.7867	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5328	Approved
0.775	Intermediate Similarity	NPD5364	Discontinued
0.7662	Intermediate Similarity	NPD5777	Approved
0.7619	Intermediate Similarity	NPD4786	Approved
0.7614	Intermediate Similarity	NPD8035	Phase 2
0.7614	Intermediate Similarity	NPD6079	Approved
0.7614	Intermediate Similarity	NPD8034	Phase 2
0.7595	Intermediate Similarity	NPD3702	Approved
0.7532	Intermediate Similarity	NPD4787	Phase 1
0.75	Intermediate Similarity	NPD4788	Approved
0.7442	Intermediate Similarity	NPD3618	Phase 1
0.7381	Intermediate Similarity	NPD3667	Approved
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD4202	Approved
0.7097	Intermediate Similarity	NPD5222	Approved
0.7097	Intermediate Similarity	NPD5221	Approved
0.7097	Intermediate Similarity	NPD4697	Phase 3
0.7097	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5173	Approved
0.7021	Intermediate Similarity	NPD4755	Approved
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3666	Approved
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.6941	Remote Similarity	NPD7525	Registered
0.6941	Remote Similarity	NPD6928	Phase 2
0.6939	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD8418	Phase 2
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.6875	Remote Similarity	NPD4700	Approved
0.6804	Remote Similarity	NPD5223	Approved
0.6774	Remote Similarity	NPD6399	Phase 3
0.6735	Remote Similarity	NPD5226	Approved
0.6735	Remote Similarity	NPD5224	Approved
0.6735	Remote Similarity	NPD5211	Phase 2
0.6735	Remote Similarity	NPD5225	Approved
0.6735	Remote Similarity	NPD4633	Approved
0.6706	Remote Similarity	NPD3617	Approved
0.67	Remote Similarity	NPD5739	Approved
0.67	Remote Similarity	NPD6920	Discontinued
0.67	Remote Similarity	NPD6402	Approved
0.67	Remote Similarity	NPD7128	Approved
0.67	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD3198	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD3668	Phase 3
0.6628	Remote Similarity	NPD7645	Phase 2
0.66	Remote Similarity	NPD5141	Approved
0.6591	Remote Similarity	NPD4221	Approved
0.6591	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD7320	Approved
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD6415	Discontinued
0.6569	Remote Similarity	NPD6899	Approved
0.6556	Remote Similarity	NPD5329	Approved
0.6548	Remote Similarity	NPD6942	Approved
0.6548	Remote Similarity	NPD7339	Approved
0.6535	Remote Similarity	NPD4768	Approved
0.6535	Remote Similarity	NPD4767	Approved
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6372	Approved
0.6505	Remote Similarity	NPD6373	Approved
0.6484	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4139	Approved
0.6477	Remote Similarity	NPD4692	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6444	Remote Similarity	NPD4197	Approved
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.642	Remote Similarity	NPD6705	Phase 1
0.6408	Remote Similarity	NPD4729	Approved
0.6408	Remote Similarity	NPD6011	Approved
0.6408	Remote Similarity	NPD5128	Approved
0.6408	Remote Similarity	NPD5168	Approved
0.6408	Remote Similarity	NPD4730	Approved
0.6381	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6869	Approved
0.6381	Remote Similarity	NPD6650	Approved
0.6381	Remote Similarity	NPD8130	Phase 1
0.6381	Remote Similarity	NPD6649	Approved
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6617	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6354	Remote Similarity	NPD7900	Approved
0.6354	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD6014	Approved
0.6346	Remote Similarity	NPD6012	Approved
0.6327	Remote Similarity	NPD6084	Phase 2
0.6327	Remote Similarity	NPD6083	Phase 2
0.6321	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD6882	Approved
0.6304	Remote Similarity	NPD4688	Approved
0.6304	Remote Similarity	NPD4689	Approved
0.6304	Remote Similarity	NPD4693	Phase 3
0.6304	Remote Similarity	NPD6684	Approved
0.6304	Remote Similarity	NPD4690	Approved
0.6304	Remote Similarity	NPD7521	Approved
0.6304	Remote Similarity	NPD4138	Approved
0.6304	Remote Similarity	NPD7146	Approved
0.6304	Remote Similarity	NPD5330	Approved
0.6304	Remote Similarity	NPD7334	Approved
0.6304	Remote Similarity	NPD5205	Approved
0.6304	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD5210	Approved
0.6289	Remote Similarity	NPD4629	Approved
0.6286	Remote Similarity	NPD5135	Approved
0.6286	Remote Similarity	NPD5247	Approved
0.6286	Remote Similarity	NPD5248	Approved
0.6286	Remote Similarity	NPD5169	Approved
0.6286	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4634	Approved
0.6286	Remote Similarity	NPD5251	Approved
0.6286	Remote Similarity	NPD5250	Approved
0.6286	Remote Similarity	NPD5249	Phase 3
0.6279	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8298	Phase 2
0.6238	Remote Similarity	NPD7632	Discontinued
0.6226	Remote Similarity	NPD5215	Approved
0.6226	Remote Similarity	NPD5217	Approved
0.6226	Remote Similarity	NPD5216	Approved
0.6226	Remote Similarity	NPD5127	Approved
0.6216	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6700	Approved
0.618	Remote Similarity	NPD4748	Discontinued
0.617	Remote Similarity	NPD6903	Approved
0.617	Remote Similarity	NPD6672	Approved
0.617	Remote Similarity	NPD5737	Approved
0.6147	Remote Similarity	NPD6868	Approved
0.6146	Remote Similarity	NPD6703	Approved
0.6146	Remote Similarity	NPD6702	Approved
0.6143	Remote Similarity	NPD384	Approved
0.6143	Remote Similarity	NPD385	Approved
0.6129	Remote Similarity	NPD4694	Approved
0.6129	Remote Similarity	NPD5690	Phase 2
0.6129	Remote Similarity	NPD5280	Approved
0.6111	Remote Similarity	NPD4632	Approved
0.6091	Remote Similarity	NPD7115	Discovery
0.6082	Remote Similarity	NPD8171	Discontinued
0.6055	Remote Similarity	NPD5167	Approved
0.6047	Remote Similarity	NPD6926	Approved
0.6047	Remote Similarity	NPD6924	Approved
0.6036	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7100	Approved
0.5982	Remote Similarity	NPD7101	Approved
0.5963	Remote Similarity	NPD8133	Approved
0.596	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD6098	Approved
0.5955	Remote Similarity	NPD4776	Phase 2
0.5955	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4777	Suspended
0.5946	Remote Similarity	NPD6009	Approved
0.5946	Remote Similarity	NPD6317	Approved
0.5943	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5696	Approved
0.5938	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6054	Approved
0.5929	Remote Similarity	NPD6059	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