NPASS Compound

Structure

NPC23884 OpenBabel07101719512D 33 37 0 0 1 0 0 0 0 0999 V2000 -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 3.5542 1.6925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8306 1.0410 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 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 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 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -0.1860 0.0000 C 0 0 2 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 -0.0000 0.0000 C 0 0 2 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 0 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 -1.6865 0.9737 0.0000 C 0 0 1 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 3.7566 0.7401 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 1 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 -2.5297 -0.4868 0.0000 O 0 0 0 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 4.7090 0.9425 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 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 28 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 30 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 6 0 0 0 19 23 1 0 0 0 0 19 29 1 6 0 0 0 20 24 1 0 0 0 0 20 31 1 1 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 32 2 0 0 0 0 23 27 1 1 0 0 0 24 25 1 0 0 0 0 24 28 1 1 0 0 0 26 33 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:	458.38
Volume:	508.388
LogP:	5.389
LogD:	5.026
LogS:	-4.655
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.949
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:	-5.101
MDCK Permeability:	2.8683116397587582e-05
Pgp-inhibitor:	0.519
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.408
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	91.8729019165039%
Volume Distribution (VD):	0.941
Pgp-substrate:	1.579569697380066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.701
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.493
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	3.963
Half-life (T1/2):	0.287

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.132
Skin Sensitization:	0.264
Carcinogencity:	0.005
Eye Corrosion:	0.443
Eye Irritation:	0.453
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC23884

Natural Product ID:	NPC23884
*Common Name:**	6Beta,20-Dihydroxylupan-3-One
IUPAC Name:	(1R,3aR,5aR,5bR,7R,7aR,11aR,11bR,13aR,13bS)-7-hydroxy-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:
Standard InCHIKey:	NUDALCNACCYYLC-MUACLIQTSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-25(2)22(32)12-14-28(6)21-10-9-19-23-18(26(3,4)33)11-13-27(23,5)15-16-29(19,7)30(21,8)17-20(31)24(25)28/h18-21,23-24,31,33H,9-17H2,1-8H3/t18-,19-,20-,21-,23-,24+,27-,28-,29-,30-/m1/s1
SMILES:	O[C@@H]1C[C@]2(C)[C@@H]([C@@]3([C@@H]1C(C)(C)C(=O)CC3)C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@@H]1[C@@H](CC2)C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581944
PubChem CID:	21672688
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
NPO32825	cassine xylocarpa	Species	Celastraceae	Eukaryota	dried stems	Ahuachapan, El Salvado	n.a.	PMID[25927586]

☑ 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	>	100000.0	nM	PMID[574023]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[574023]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	7000.0	nM	PMID[574023]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	14.3	n.a.	PMID[574023]

☑ 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 NPC23884 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	344
0.1-0.2	3383
0.2-0.3	14102
0.3-0.4	10808
0.4-0.5	5427
0.5-0.6	4626
0.6-0.7	2922
0.7-0.8	880
0.8-0.85	126
0.85-0.9	61
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC195155
0.9718	High Similarity	NPC97534
0.9718	High Similarity	NPC174964
0.9583	High Similarity	NPC5767
0.9583	High Similarity	NPC475742
0.9452	High Similarity	NPC221420
0.9437	High Similarity	NPC232112
0.9315	High Similarity	NPC472486
0.9315	High Similarity	NPC472487
0.9296	High Similarity	NPC156277
0.9296	High Similarity	NPC151018
0.9296	High Similarity	NPC58057
0.9296	High Similarity	NPC320549
0.9296	High Similarity	NPC89310
0.9189	High Similarity	NPC298168
0.9189	High Similarity	NPC143133
0.9189	High Similarity	NPC475031
0.9178	High Similarity	NPC273366
0.9178	High Similarity	NPC21220
0.9178	High Similarity	NPC125767
0.9041	High Similarity	NPC159325
0.9041	High Similarity	NPC254340
0.9041	High Similarity	NPC168511
0.9014	High Similarity	NPC6120
0.9014	High Similarity	NPC327728
0.9014	High Similarity	NPC213178
0.9014	High Similarity	NPC131892
0.8919	High Similarity	NPC212733
0.8904	High Similarity	NPC68426
0.8904	High Similarity	NPC81759
0.8904	High Similarity	NPC477229
0.8904	High Similarity	NPC282905
0.8873	High Similarity	NPC473225
0.8861	High Similarity	NPC475745
0.8861	High Similarity	NPC474482
0.8861	High Similarity	NPC474996
0.8846	High Similarity	NPC30583
0.8846	High Similarity	NPC61107
0.8846	High Similarity	NPC268040
0.8846	High Similarity	NPC289486
0.88	High Similarity	NPC108840
0.88	High Similarity	NPC4209
0.8784	High Similarity	NPC280026
0.8784	High Similarity	NPC167702
0.8734	High Similarity	NPC472743
0.8734	High Similarity	NPC475726
0.8732	High Similarity	NPC48079
0.8718	High Similarity	NPC50658
0.8718	High Similarity	NPC58631
0.8701	High Similarity	NPC320144
0.8684	High Similarity	NPC207010
0.8684	High Similarity	NPC317913
0.8667	High Similarity	NPC267753
0.8667	High Similarity	NPC159789
0.8649	High Similarity	NPC310766
0.8642	High Similarity	NPC472738
0.8611	High Similarity	NPC472741
0.8608	High Similarity	NPC328007
0.8608	High Similarity	NPC317066
0.8592	High Similarity	NPC142712
0.859	High Similarity	NPC261616
0.859	High Similarity	NPC470609
0.8571	High Similarity	NPC224802
0.8571	High Similarity	NPC80089
0.8571	High Similarity	NPC171426
0.8571	High Similarity	NPC34046
0.8571	High Similarity	NPC324700
0.8571	High Similarity	NPC185465
0.8533	High Similarity	NPC130011
0.8533	High Similarity	NPC472854
0.8533	High Similarity	NPC133922
0.8519	High Similarity	NPC292553
0.85	High Similarity	NPC327451
0.8493	Intermediate Similarity	NPC254037
0.8493	Intermediate Similarity	NPC129829
0.8493	Intermediate Similarity	NPC324607
0.8493	Intermediate Similarity	NPC321732
0.8481	Intermediate Similarity	NPC12933
0.8481	Intermediate Similarity	NPC48756
0.8481	Intermediate Similarity	NPC280781
0.8481	Intermediate Similarity	NPC469745
0.8462	Intermediate Similarity	NPC201276
0.8462	Intermediate Similarity	NPC80891
0.8442	Intermediate Similarity	NPC264602
0.8434	Intermediate Similarity	NPC472739
0.8434	Intermediate Similarity	NPC474719
0.8395	Intermediate Similarity	NPC34984
0.8395	Intermediate Similarity	NPC74595
0.8395	Intermediate Similarity	NPC50438
0.8395	Intermediate Similarity	NPC264665
0.8395	Intermediate Similarity	NPC25037
0.8395	Intermediate Similarity	NPC474233
0.8378	Intermediate Similarity	NPC192192
0.8378	Intermediate Similarity	NPC231945
0.8378	Intermediate Similarity	NPC108131
0.8356	Intermediate Similarity	NPC103647
0.8356	Intermediate Similarity	NPC180777
0.8356	Intermediate Similarity	NPC260319
0.8356	Intermediate Similarity	NPC2568
0.8333	Intermediate Similarity	NPC472608
0.8313	Intermediate Similarity	NPC4643
0.8313	Intermediate Similarity	NPC57469
0.8293	Intermediate Similarity	NPC264317
0.8293	Intermediate Similarity	NPC294438
0.8267	Intermediate Similarity	NPC127094
0.8267	Intermediate Similarity	NPC247195
0.8267	Intermediate Similarity	NPC473267
0.8243	Intermediate Similarity	NPC476734
0.8243	Intermediate Similarity	NPC319671
0.8243	Intermediate Similarity	NPC252032
0.8243	Intermediate Similarity	NPC469941
0.8243	Intermediate Similarity	NPC196197
0.8228	Intermediate Similarity	NPC201459
0.8219	Intermediate Similarity	NPC472984
0.8193	Intermediate Similarity	NPC476727
0.8193	Intermediate Similarity	NPC98236
0.8193	Intermediate Similarity	NPC269396
0.8193	Intermediate Similarity	NPC476726
0.8193	Intermediate Similarity	NPC80700
0.8193	Intermediate Similarity	NPC2783
0.8193	Intermediate Similarity	NPC12774
0.8182	Intermediate Similarity	NPC72444
0.8182	Intermediate Similarity	NPC27349
0.8182	Intermediate Similarity	NPC24014
0.8171	Intermediate Similarity	NPC471044
0.8171	Intermediate Similarity	NPC105895
0.8171	Intermediate Similarity	NPC473336
0.8169	Intermediate Similarity	NPC114891
0.8148	Intermediate Similarity	NPC121121
0.8133	Intermediate Similarity	NPC477929
0.8133	Intermediate Similarity	NPC476731
0.8133	Intermediate Similarity	NPC282454
0.8125	Intermediate Similarity	NPC477851
0.8118	Intermediate Similarity	NPC61688
0.8118	Intermediate Similarity	NPC122116
0.8108	Intermediate Similarity	NPC475977
0.8108	Intermediate Similarity	NPC474954
0.8101	Intermediate Similarity	NPC329117
0.8101	Intermediate Similarity	NPC26029
0.8095	Intermediate Similarity	NPC263802
0.8095	Intermediate Similarity	NPC269360
0.8095	Intermediate Similarity	NPC33768
0.8095	Intermediate Similarity	NPC202937
0.8095	Intermediate Similarity	NPC264005
0.8095	Intermediate Similarity	NPC252714
0.8072	Intermediate Similarity	NPC62572
0.8072	Intermediate Similarity	NPC76518
0.8052	Intermediate Similarity	NPC477508
0.8049	Intermediate Similarity	NPC472744
0.8046	Intermediate Similarity	NPC244356
0.8046	Intermediate Similarity	NPC224060
0.8028	Intermediate Similarity	NPC71460
0.8028	Intermediate Similarity	NPC148174
0.8028	Intermediate Similarity	NPC218585
0.8026	Intermediate Similarity	NPC109457
0.8026	Intermediate Similarity	NPC290058
0.8026	Intermediate Similarity	NPC157422
0.8026	Intermediate Similarity	NPC473279
0.8026	Intermediate Similarity	NPC126642
0.8026	Intermediate Similarity	NPC100586
0.8025	Intermediate Similarity	NPC103754
0.8025	Intermediate Similarity	NPC474484
0.8025	Intermediate Similarity	NPC476071
0.8023	Intermediate Similarity	NPC46758
0.8	Intermediate Similarity	NPC241085
0.8	Intermediate Similarity	NPC31302
0.8	Intermediate Similarity	NPC471900
0.8	Intermediate Similarity	NPC193360
0.8	Intermediate Similarity	NPC220379
0.8	Intermediate Similarity	NPC107919
0.8	Intermediate Similarity	NPC470830
0.8	Intermediate Similarity	NPC299948
0.8	Intermediate Similarity	NPC66407
0.8	Intermediate Similarity	NPC245029
0.8	Intermediate Similarity	NPC16377
0.7976	Intermediate Similarity	NPC471737
0.7976	Intermediate Similarity	NPC472272
0.7975	Intermediate Similarity	NPC477919
0.7975	Intermediate Similarity	NPC472746
0.7975	Intermediate Similarity	NPC180199
0.7973	Intermediate Similarity	NPC475884
0.7973	Intermediate Similarity	NPC473230
0.7952	Intermediate Similarity	NPC473299
0.7952	Intermediate Similarity	NPC319909
0.7952	Intermediate Similarity	NPC146683
0.7949	Intermediate Similarity	NPC472311
0.7945	Intermediate Similarity	NPC260116
0.7945	Intermediate Similarity	NPC41577
0.7945	Intermediate Similarity	NPC80463
0.7945	Intermediate Similarity	NPC473276
0.7945	Intermediate Similarity	NPC474380
0.7927	Intermediate Similarity	NPC145143
0.7922	Intermediate Similarity	NPC474123
0.7907	Intermediate Similarity	NPC213832
0.7907	Intermediate Similarity	NPC220498
0.7907	Intermediate Similarity	NPC57954
0.7901	Intermediate Similarity	NPC164999
0.7895	Intermediate Similarity	NPC477850
0.7875	Intermediate Similarity	NPC478128
0.7875	Intermediate Similarity	NPC243594

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 NPC23884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	3660
0.2-0.3	3604
0.3-0.4	917
0.4-0.5	217
0.5-0.6	197
0.6-0.7	131
0.7-0.8	19
0.8-0.85	12
0.85-0.9	8
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9296	High Similarity	NPD4809	Clinical (unspecified phase)
0.9296	High Similarity	NPD4808	Clinical (unspecified phase)
0.9014	High Similarity	NPD3699	Clinical (unspecified phase)
0.9014	High Similarity	NPD3700	Clinical (unspecified phase)
0.8873	High Similarity	NPD5361	Clinical (unspecified phase)
0.8873	High Similarity	NPD5360	Phase 3
0.88	High Similarity	NPD6117	Approved
0.8784	High Similarity	NPD6113	Clinical (unspecified phase)
0.8684	High Similarity	NPD6116	Phase 1
0.8667	High Similarity	NPD3703	Phase 2
0.863	High Similarity	NPD4244	Approved
0.863	High Similarity	NPD4789	Approved
0.863	High Similarity	NPD4245	Approved
0.8571	High Similarity	NPD6115	Approved
0.8571	High Similarity	NPD6118	Approved
0.8571	High Similarity	NPD6114	Approved
0.8571	High Similarity	NPD6697	Approved
0.8493	Intermediate Similarity	NPD3698	Phase 2
0.8451	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD4758	Discontinued
0.8101	Intermediate Similarity	NPD3671	Phase 1
0.8	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5364	Discontinued
0.7838	Intermediate Similarity	NPD4224	Phase 2
0.7792	Intermediate Similarity	NPD6081	Approved
0.7727	Intermediate Similarity	NPD8035	Phase 2
0.7727	Intermediate Similarity	NPD8034	Phase 2
0.7662	Intermediate Similarity	NPD4787	Phase 1
0.7619	Intermediate Similarity	NPD4788	Approved
0.7564	Intermediate Similarity	NPD5777	Approved
0.7558	Intermediate Similarity	NPD3618	Phase 1
0.7529	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD3702	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7333	Intermediate Similarity	NPD6079	Approved
0.7294	Intermediate Similarity	NPD3667	Approved
0.7253	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD7525	Registered
0.7021	Intermediate Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD4755	Approved
0.6932	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD3133	Approved
0.6932	Remote Similarity	NPD3666	Approved
0.6882	Remote Similarity	NPD6399	Phase 3
0.686	Remote Similarity	NPD6928	Phase 2
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6809	Remote Similarity	NPD7748	Approved
0.6804	Remote Similarity	NPD5286	Approved
0.6804	Remote Similarity	NPD4696	Approved
0.6804	Remote Similarity	NPD4700	Approved
0.6804	Remote Similarity	NPD8418	Phase 2
0.6804	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD6920	Discontinued
0.6778	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5173	Approved
0.6771	Remote Similarity	NPD7902	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6735	Remote Similarity	NPD5223	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6705	Remote Similarity	NPD4221	Approved
0.67	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6634	Remote Similarity	NPD6402	Approved
0.6634	Remote Similarity	NPD7128	Approved
0.6634	Remote Similarity	NPD5739	Approved
0.6634	Remote Similarity	NPD6675	Approved
0.6628	Remote Similarity	NPD3617	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.6602	Remote Similarity	NPD6372	Approved
0.66	Remote Similarity	NPD5174	Approved
0.66	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD5175	Approved
0.6593	Remote Similarity	NPD5279	Phase 3
0.6591	Remote Similarity	NPD4692	Approved
0.6591	Remote Similarity	NPD4139	Approved
0.6579	Remote Similarity	NPD3198	Approved
0.6562	Remote Similarity	NPD5210	Approved
0.6562	Remote Similarity	NPD4629	Approved
0.6556	Remote Similarity	NPD3668	Phase 3
0.6556	Remote Similarity	NPD4197	Approved
0.6552	Remote Similarity	NPD7645	Phase 2
0.6535	Remote Similarity	NPD5141	Approved
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.6505	Remote Similarity	NPD6415	Discontinued
0.6505	Remote Similarity	NPD7320	Approved
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6458	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7900	Approved
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD4689	Approved
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD4688	Approved
0.6408	Remote Similarity	NPD5697	Approved
0.6408	Remote Similarity	NPD5701	Approved
0.6381	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD7290	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD7638	Approved
0.6346	Remote Similarity	NPD6011	Approved
0.6346	Remote Similarity	NPD4729	Approved
0.6346	Remote Similarity	NPD4730	Approved
0.6346	Remote Similarity	NPD5128	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.633	Remote Similarity	NPD7115	Discovery
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8130	Phase 1
0.6321	Remote Similarity	NPD6847	Approved
0.63	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD7639	Approved
0.6292	Remote Similarity	NPD4748	Discontinued
0.6286	Remote Similarity	NPD6014	Approved
0.6286	Remote Similarity	NPD6013	Approved
0.6286	Remote Similarity	NPD6012	Approved
0.6262	Remote Similarity	NPD6882	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD4694	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD5690	Phase 2
0.6237	Remote Similarity	NPD5280	Approved
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6226	Remote Similarity	NPD5251	Approved
0.6226	Remote Similarity	NPD5249	Phase 3
0.6226	Remote Similarity	NPD5169	Approved
0.6226	Remote Similarity	NPD5135	Approved
0.6226	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4634	Approved
0.6226	Remote Similarity	NPD5247	Approved
0.6226	Remote Similarity	NPD5248	Approved
0.6226	Remote Similarity	NPD5250	Approved
0.6224	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD5168	Approved
0.6176	Remote Similarity	NPD7632	Discontinued
0.6168	Remote Similarity	NPD5215	Approved
0.6168	Remote Similarity	NPD5217	Approved
0.6168	Remote Similarity	NPD5127	Approved
0.6168	Remote Similarity	NPD5216	Approved
0.6163	Remote Similarity	NPD6926	Approved
0.6163	Remote Similarity	NPD6924	Approved
0.6146	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6700	Approved
0.6133	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6903	Approved
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD5737	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
0.6064	Remote Similarity	NPD6098	Approved
0.6061	Remote Similarity	NPD5695	Phase 3
0.6056	Remote Similarity	NPD384	Approved
0.6056	Remote Similarity	NPD385	Approved
0.6055	Remote Similarity	NPD8133	Approved
0.6055	Remote Similarity	NPD4632	Approved
0.6055	Remote Similarity	NPD8298	Phase 2
0.6038	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6933	Approved
0.602	Remote Similarity	NPD8171	Discontinued
0.6	Remote Similarity	NPD5167	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD6008	Approved
0.5982	Remote Similarity	NPD6335	Approved
0.5981	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6001	Approved
0.5946	Remote Similarity	NPD6274	Approved
0.5946	Remote Similarity	NPD6868	Approved
0.5946	Remote Similarity	NPD6940	Discontinued
0.5943	Remote Similarity	NPD6412	Phase 2
0.593	Remote Similarity	NPD4243	Approved
0.5929	Remote Similarity	NPD7100	Approved
0.5929	Remote Similarity	NPD7101	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