NPASS Compound

Structure

NPC183380 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 26 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 1 1 6 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 14 23 2 0 0 0 0 15 11 1 6 0 0 0 15 19 1 0 0 0 0 15 34 1 0 0 0 0 16 25 1 0 0 0 0 16 26 1 1 0 0 0 17 25 1 0 0 0 0 17 29 1 1 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 30 1 1 0 0 0 20 23 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 6 0 0 0 22 24 1 0 0 0 0 22 33 1 1 0 0 0 23 35 1 0 0 0 0 24 34 1 0 0 0 0 24 35 1 6 0 0 0 26 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.27
Volume:	495.229
LogP:	1.337
LogD:	1.387
LogS:	-3.375
# Rotatable Bonds:	5
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.794
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.881
MDCK Permeability:	9.016066542244516e-06
Pgp-inhibitor:	0.14
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.329
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	73.07506561279297%
Volume Distribution (VD):	0.352
Pgp-substrate:	20.63654136657715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.673
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.275
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	3.496
Half-life (T1/2):	0.584

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.354
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.826
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC183380

Natural Product ID:	NPC183380
*Common Name:**	(2S,3R,4S,5S,6R)-2-[[(4Bs,7S,8Ar)-4,7-Dihydroxy-2-[(2S)-1-Hydroxypropan-2-Yl]-4B,8,8-Trimethyl-5,6,7,8A,9,10-Hexahydrophenanthren-3-Yl]Oxy]-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(4bS,7S,8aR)-4,7-dihydroxy-2-[(2S)-1-hydroxypropan-2-yl]-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	IACPYMAYLYRWCN-VXAYKVKJSA-N
Standard InCHI:	InChI=1S/C26H40O9/c1-12(10-27)14-9-13-5-6-16-25(2,3)17(29)7-8-26(16,4)18(13)20(31)23(14)35-24-22(33)21(32)19(30)15(11-28)34-24/h9,12,15-17,19,21-22,24,27-33H,5-8,10-11H2,1-4H3/t12-,15-,16+,17+,19-,21+,22-,24+,26+/m1/s1
SMILES:	C[C@H](CO)c1cc2CC[C@H]3C(C)(C)[C@H](CC[C@]3(C)c2c(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523355
PubChem CID:	24879399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	>	10000.0	nM	PMID[549590]
NPT2511	Cell Line	HGC-27	Homo sapiens	IC50	>	10000.0	nM	PMID[549590]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	10000.0	nM	PMID[549590]

☑ 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 NPC183380 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	482
0.1-0.2	1570
0.2-0.3	3693
0.3-0.4	8067
0.4-0.5	9235
0.5-0.6	6763
0.6-0.7	8592
0.7-0.8	3802
0.8-0.85	382
0.85-0.9	84
0.9-0.95	21
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC200645
0.9793	High Similarity	NPC106669
0.9793	High Similarity	NPC475227
0.9583	High Similarity	NPC179809
0.9577	High Similarity	NPC164183
0.9577	High Similarity	NPC133251
0.9384	High Similarity	NPC44452
0.9384	High Similarity	NPC474893
0.9384	High Similarity	NPC475940
0.9384	High Similarity	NPC220006
0.9384	High Similarity	NPC181452
0.9315	High Similarity	NPC291326
0.9315	High Similarity	NPC474940
0.9315	High Similarity	NPC474795
0.9315	High Similarity	NPC303013
0.9315	High Similarity	NPC474834
0.9315	High Similarity	NPC117788
0.9315	High Similarity	NPC159697
0.9315	High Similarity	NPC290902
0.9315	High Similarity	NPC474856
0.9315	High Similarity	NPC130959
0.9241	High Similarity	NPC286245
0.9241	High Similarity	NPC272619
0.9221	High Similarity	NPC25889
0.9189	High Similarity	NPC225815
0.9189	High Similarity	NPC469706
0.9189	High Similarity	NPC182368
0.9189	High Similarity	NPC145979
0.9189	High Similarity	NPC260781
0.9189	High Similarity	NPC9933
0.9189	High Similarity	NPC214326
0.9189	High Similarity	NPC218041
0.9189	High Similarity	NPC185955
0.9189	High Similarity	NPC469707
0.9172	High Similarity	NPC253015
0.9172	High Similarity	NPC471065
0.9116	High Similarity	NPC213074
0.9116	High Similarity	NPC275284
0.9116	High Similarity	NPC193473
0.9116	High Similarity	NPC224674
0.9116	High Similarity	NPC114505
0.9116	High Similarity	NPC15956
0.9116	High Similarity	NPC31325
0.9085	High Similarity	NPC68292
0.9067	High Similarity	NPC21902
0.9067	High Similarity	NPC474442
0.898	High Similarity	NPC43508
0.898	High Similarity	NPC476301
0.8933	High Similarity	NPC472710
0.8933	High Similarity	NPC472709
0.8933	High Similarity	NPC98624
0.8912	High Similarity	NPC79429
0.8912	High Similarity	NPC217635
0.8912	High Similarity	NPC471667
0.8874	High Similarity	NPC2745
0.8873	High Similarity	NPC227719
0.8844	High Similarity	NPC470950
0.8844	High Similarity	NPC185307
0.8816	High Similarity	NPC157783
0.8808	High Similarity	NPC195561
0.8808	High Similarity	NPC158784
0.8784	High Similarity	NPC283995
0.8784	High Similarity	NPC470235
0.8784	High Similarity	NPC129417
0.8776	High Similarity	NPC476356
0.8776	High Similarity	NPC253878
0.8767	High Similarity	NPC106944
0.8759	High Similarity	NPC470413
0.8759	High Similarity	NPC138738
0.8758	High Similarity	NPC78809
0.875	High Similarity	NPC302915
0.8732	High Similarity	NPC312341
0.8725	High Similarity	NPC38041
0.8725	High Similarity	NPC475096
0.8725	High Similarity	NPC277867
0.8725	High Similarity	NPC161700
0.8725	High Similarity	NPC279298
0.8725	High Similarity	NPC22150
0.8718	High Similarity	NPC478269
0.8716	High Similarity	NPC46092
0.8716	High Similarity	NPC113680
0.8716	High Similarity	NPC278961
0.8707	High Similarity	NPC471414
0.8707	High Similarity	NPC472711
0.8693	High Similarity	NPC325860
0.869	High Similarity	NPC52277
0.869	High Similarity	NPC199459
0.869	High Similarity	NPC177035
0.8675	High Similarity	NPC212142
0.8675	High Similarity	NPC270751
0.8675	High Similarity	NPC473876
0.8671	High Similarity	NPC59239
0.8667	High Similarity	NPC99515
0.8667	High Similarity	NPC112861
0.8667	High Similarity	NPC125755
0.8667	High Similarity	NPC190714
0.8658	High Similarity	NPC473845
0.8649	High Similarity	NPC48309
0.8649	High Similarity	NPC5262
0.8649	High Similarity	NPC60249
0.8649	High Similarity	NPC472714
0.863	High Similarity	NPC304152
0.8609	High Similarity	NPC474397
0.8609	High Similarity	NPC39657
0.8609	High Similarity	NPC227902
0.8608	High Similarity	NPC478267
0.86	High Similarity	NPC90645
0.86	High Similarity	NPC18979
0.86	High Similarity	NPC472457
0.8598	High Similarity	NPC475054
0.8591	High Similarity	NPC37793
0.8591	High Similarity	NPC477898
0.859	High Similarity	NPC228357
0.8581	High Similarity	NPC76871
0.8571	High Similarity	NPC476452
0.8562	High Similarity	NPC475224
0.8553	High Similarity	NPC130449
0.8553	High Similarity	NPC175976
0.8553	High Similarity	NPC95990
0.8553	High Similarity	NPC248132
0.8552	High Similarity	NPC476411
0.8552	High Similarity	NPC187194
0.8552	High Similarity	NPC35731
0.8544	High Similarity	NPC1253
0.8544	High Similarity	NPC100936
0.8543	High Similarity	NPC233980
0.8533	High Similarity	NPC168579
0.8533	High Similarity	NPC472712
0.8533	High Similarity	NPC473108
0.8533	High Similarity	NPC138227
0.8533	High Similarity	NPC471063
0.8533	High Similarity	NPC118385
0.8533	High Similarity	NPC472713
0.8533	High Similarity	NPC84181
0.8533	High Similarity	NPC187774
0.8533	High Similarity	NPC25292
0.8533	High Similarity	NPC469313
0.8533	High Similarity	NPC473045
0.8533	High Similarity	NPC76176
0.8533	High Similarity	NPC473046
0.8531	High Similarity	NPC99795
0.8523	High Similarity	NPC189115
0.8523	High Similarity	NPC469559
0.8523	High Similarity	NPC246947
0.8523	High Similarity	NPC475084
0.8521	High Similarity	NPC201069
0.8497	Intermediate Similarity	NPC286235
0.8497	Intermediate Similarity	NPC51328
0.8497	Intermediate Similarity	NPC55158
0.8493	Intermediate Similarity	NPC79957
0.8487	Intermediate Similarity	NPC15538
0.8487	Intermediate Similarity	NPC473480
0.8481	Intermediate Similarity	NPC185231
0.8472	Intermediate Similarity	NPC65942
0.8472	Intermediate Similarity	NPC248307
0.8467	Intermediate Similarity	NPC472451
0.8467	Intermediate Similarity	NPC473044
0.8456	Intermediate Similarity	NPC210192
0.8456	Intermediate Similarity	NPC35216
0.8456	Intermediate Similarity	NPC265075
0.8456	Intermediate Similarity	NPC469661
0.8452	Intermediate Similarity	NPC134911
0.8452	Intermediate Similarity	NPC46283
0.8452	Intermediate Similarity	NPC322899
0.8452	Intermediate Similarity	NPC160196
0.8452	Intermediate Similarity	NPC469944
0.8452	Intermediate Similarity	NPC44192
0.8452	Intermediate Similarity	NPC226108
0.8452	Intermediate Similarity	NPC302610
0.8452	Intermediate Similarity	NPC272552
0.8446	Intermediate Similarity	NPC230124
0.8446	Intermediate Similarity	NPC114171
0.8446	Intermediate Similarity	NPC6300
0.8442	Intermediate Similarity	NPC477612
0.8442	Intermediate Similarity	NPC24425
0.8435	Intermediate Similarity	NPC29799
0.8435	Intermediate Similarity	NPC263367
0.8435	Intermediate Similarity	NPC10737
0.8435	Intermediate Similarity	NPC54743
0.8435	Intermediate Similarity	NPC156502
0.8435	Intermediate Similarity	NPC477939
0.8435	Intermediate Similarity	NPC209985
0.8435	Intermediate Similarity	NPC177160
0.8431	Intermediate Similarity	NPC226153
0.8431	Intermediate Similarity	NPC304048
0.8431	Intermediate Similarity	NPC280945
0.8425	Intermediate Similarity	NPC478085
0.8425	Intermediate Similarity	NPC311256
0.8425	Intermediate Similarity	NPC87696
0.8421	Intermediate Similarity	NPC471608
0.8421	Intermediate Similarity	NPC260397
0.8421	Intermediate Similarity	NPC205796
0.8421	Intermediate Similarity	NPC276753
0.8421	Intermediate Similarity	NPC112251
0.8414	Intermediate Similarity	NPC321086
0.8411	Intermediate Similarity	NPC50250
0.8403	Intermediate Similarity	NPC80600
0.8403	Intermediate Similarity	NPC472024
0.84	Intermediate Similarity	NPC302506
0.84	Intermediate Similarity	NPC186033

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 NPC183380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	880
0.2-0.3	1911
0.3-0.4	2839
0.4-0.5	1696
0.5-0.6	926
0.6-0.7	432
0.7-0.8	84
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9366	High Similarity	NPD6674	Discontinued
0.8232	Intermediate Similarity	NPD7228	Approved
0.8041	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3620	Phase 2
0.8025	Intermediate Similarity	NPD6234	Discontinued
0.7937	Intermediate Similarity	NPD37	Approved
0.7919	Intermediate Similarity	NPD1613	Approved
0.7919	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4965	Approved
0.7901	Intermediate Similarity	NPD4967	Phase 2
0.7901	Intermediate Similarity	NPD4966	Approved
0.7857	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7266	Discontinued
0.7799	Intermediate Similarity	NPD1653	Approved
0.7785	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7240	Approved
0.7718	Intermediate Similarity	NPD3027	Phase 3
0.7706	Intermediate Similarity	NPD7074	Phase 3
0.7703	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD8455	Phase 2
0.7667	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3705	Approved
0.7655	Intermediate Similarity	NPD1091	Approved
0.7651	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7054	Approved
0.7632	Intermediate Similarity	NPD5735	Approved
0.763	Intermediate Similarity	NPD8313	Approved
0.763	Intermediate Similarity	NPD8312	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7602	Intermediate Similarity	NPD7472	Approved
0.7566	Intermediate Similarity	NPD4060	Phase 1
0.7544	Intermediate Similarity	NPD5844	Phase 1
0.7533	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD6696	Suspended
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7471	Intermediate Similarity	NPD2489	Approved
0.7471	Intermediate Similarity	NPD27	Approved
0.7467	Intermediate Similarity	NPD2861	Phase 2
0.7458	Intermediate Similarity	NPD7906	Approved
0.7456	Intermediate Similarity	NPD3051	Approved
0.7443	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7310	Approved
0.7429	Intermediate Similarity	NPD7311	Approved
0.7429	Intermediate Similarity	NPD7313	Approved
0.7429	Intermediate Similarity	NPD7312	Approved
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7251	Discontinued
0.7412	Intermediate Similarity	NPD2969	Approved
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD2970	Approved
0.7401	Intermediate Similarity	NPD4663	Approved
0.74	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5126	Approved
0.7397	Intermediate Similarity	NPD5125	Phase 3
0.7391	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5762	Approved
0.7389	Intermediate Similarity	NPD5763	Approved
0.7386	Intermediate Similarity	NPD7309	Approved
0.7384	Intermediate Similarity	NPD3818	Discontinued
0.7377	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7808	Phase 3
0.7365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6797	Phase 2
0.7338	Intermediate Similarity	NPD4140	Approved
0.733	Intermediate Similarity	NPD4577	Approved
0.733	Intermediate Similarity	NPD4578	Approved
0.7329	Intermediate Similarity	NPD1357	Approved
0.7315	Intermediate Similarity	NPD4749	Approved
0.7315	Intermediate Similarity	NPD5327	Phase 3
0.7314	Intermediate Similarity	NPD6559	Discontinued
0.7308	Intermediate Similarity	NPD7097	Phase 1
0.7292	Intermediate Similarity	NPD7157	Approved
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5058	Phase 3
0.7267	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6166	Phase 2
0.7246	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7340	Approved
0.7241	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7473	Discontinued
0.7219	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3094	Phase 2
0.7219	Intermediate Similarity	NPD7680	Approved
0.7216	Intermediate Similarity	NPD7685	Pre-registration
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD6100	Approved
0.7186	Intermediate Similarity	NPD1934	Approved
0.7181	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD3657	Discovery
0.7152	Intermediate Similarity	NPD4108	Discontinued
0.7151	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4097	Suspended
0.7134	Intermediate Similarity	NPD6353	Approved
0.7108	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD7985	Registered
0.7095	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6959	Discontinued
0.7089	Intermediate Similarity	NPD4538	Approved
0.7089	Intermediate Similarity	NPD4536	Approved
0.7089	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6841	Approved
0.7072	Intermediate Similarity	NPD6843	Phase 3
0.7072	Intermediate Similarity	NPD6842	Approved
0.707	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5124	Phase 1
0.7067	Intermediate Similarity	NPD3092	Approved
0.7063	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6071	Discontinued
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7041	Intermediate Similarity	NPD1465	Phase 2
0.7037	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7037	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4110	Phase 3
0.7037	Intermediate Similarity	NPD4628	Phase 3
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7034	Intermediate Similarity	NPD1398	Phase 1
0.7032	Intermediate Similarity	NPD7095	Approved
0.703	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7831	Phase 2
0.7018	Intermediate Similarity	NPD7833	Phase 2
0.7018	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD228	Approved
0.7012	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7041	Phase 2
0.7012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2560	Approved
0.7	Intermediate Similarity	NPD2563	Approved
0.6994	Remote Similarity	NPD2677	Approved
0.6971	Remote Similarity	NPD4481	Phase 3
0.697	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7843	Approved
0.6964	Remote Similarity	NPD7028	Phase 2
0.6939	Remote Similarity	NPD6671	Approved
0.6937	Remote Similarity	NPD5588	Approved
0.6937	Remote Similarity	NPD5960	Phase 3
0.6936	Remote Similarity	NPD4666	Phase 3
0.6933	Remote Similarity	NPD4626	Approved
0.6919	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3091	Approved
0.6902	Remote Similarity	NPD2488	Approved
0.6902	Remote Similarity	NPD2490	Approved
0.6901	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6823	Phase 2
0.6893	Remote Similarity	NPD3751	Discontinued
0.6879	Remote Similarity	NPD5709	Phase 3
0.6878	Remote Similarity	NPD6778	Approved
0.6878	Remote Similarity	NPD6781	Approved
0.6878	Remote Similarity	NPD6776	Approved
0.6878	Remote Similarity	NPD6779	Approved
0.6878	Remote Similarity	NPD6780	Approved
0.6878	Remote Similarity	NPD6782	Approved
0.6878	Remote Similarity	NPD6777	Approved
0.6872	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7783	Phase 2
0.6867	Remote Similarity	NPD5691	Approved
0.6864	Remote Similarity	NPD4380	Phase 2
0.6859	Remote Similarity	NPD7435	Discontinued
0.6856	Remote Similarity	NPD8151	Discontinued
0.6855	Remote Similarity	NPD6355	Discontinued
0.6852	Remote Similarity	NPD1375	Discontinued
0.6842	Remote Similarity	NPD2494	Approved
0.6842	Remote Similarity	NPD7819	Suspended
0.6842	Remote Similarity	NPD2977	Approved
0.6842	Remote Similarity	NPD2493	Approved
0.6842	Remote Similarity	NPD2801	Approved
0.6842	Remote Similarity	NPD5929	Approved
0.6842	Remote Similarity	NPD2978	Approved
0.6839	Remote Similarity	NPD4624	Approved
0.6839	Remote Similarity	NPD5494	Approved
0.6832	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6331	Phase 2
0.6826	Remote Similarity	NPD6273	Approved
0.6823	Remote Similarity	NPD4582	Approved
0.6823	Remote Similarity	NPD4583	Approved
0.6821	Remote Similarity	NPD7075	Discontinued
0.6813	Remote Similarity	NPD8053	Approved
0.6813	Remote Similarity	NPD8054	Approved
0.6806	Remote Similarity	NPD2684	Approved
0.68	Remote Similarity	NPD7741	Discontinued
0.68	Remote Similarity	NPD1548	Phase 1
0.6795	Remote Similarity	NPD3018	Phase 2
0.6795	Remote Similarity	NPD5736	Approved
0.6792	Remote Similarity	NPD1558	Phase 1
0.679	Remote Similarity	NPD2438	Suspended
0.6788	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5722	Discontinued
0.6772	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6798	Discontinued

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