NPASS Compound

Structure

CID1882 OpenBabel06191715322D 25 29 0 0 1 0 0 0 0 0999 V2000 3.0020 -1.9970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9168 -2.1383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5967 -2.7657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8105 -3.2754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.8075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3831 -2.3117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8104 -2.3117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6209 -1.8716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0578 -0.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8104 -0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0889 -1.9970 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6210 -2.8075 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5967 -0.9498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7463 -1.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7855 -0.0616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8104 -0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3831 -1.4038 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8104 -1.4037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8105 -1.4037 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2028 -0.6128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1780 0.6131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5968 -0.0139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6886 0.0333 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 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 8 12 1 0 0 0 0 9 18 1 0 0 0 0 9 24 1 0 0 0 0 10 19 1 0 0 0 0 10 25 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 4 1 6 0 0 0 13 19 1 1 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 2 1 6 0 0 0 19 7 1 1 0 0 0 20 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	347.736
LogP:	2.866
LogD:	2.845
LogS:	-4.472
# Rotatable Bonds:	0
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	6.485
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.157
MDCK Permeability:	2.5087558242375962e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.843
Plasma Protein Binding (PPB):	65.29440307617188%
Volume Distribution (VD):	0.866
Pgp-substrate:	34.49826431274414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.817
CYP2C19-inhibitor:	0.252
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.103
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.553

ADMET: Excretion

Clearance (CL):	8.864
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.393
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.731
Skin Sensitization:	0.04
Carcinogencity:	0.616
Eye Corrosion:	0.035
Eye Irritation:	0.62
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC1882

Natural Product ID:	NPC1882
*Common Name:**	Guidongnin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KVVWTQICVCAEKK-VWGMWKOWSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-11-12-4-5-13-19(10-25-17(23)20(13,8-12)15(11)21)7-3-6-18(2)9-24-16(22)14(18)19/h11-14H,3-10H2,1-2H3/t11-,12-,13+,14-,18+,19-,20+/m1/s1
SMILES:	C[C@@H]1[C@@H]2CC[C@H]3[C@@]4(CCC[C@@]5(C)COC(=O)[C@@H]45)COC(=O)[C@]3(C2)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455057
PubChem CID:	12067305
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575445]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20521771]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[515674]

☑ 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 NPC1882 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	411
0.1-0.2	4039
0.2-0.3	11618
0.3-0.4	11865
0.4-0.5	6170
0.5-0.6	6267
0.6-0.7	1864
0.7-0.8	414
0.8-0.85	41
0.85-0.9	2
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9241	High Similarity	NPC51135
0.9241	High Similarity	NPC101138
0.9241	High Similarity	NPC25802
0.9241	High Similarity	NPC82492
0.8916	High Similarity	NPC200580
0.8315	Intermediate Similarity	NPC193785
0.8312	Intermediate Similarity	NPC248567
0.8293	Intermediate Similarity	NPC13494
0.8182	Intermediate Similarity	NPC197701
0.8125	Intermediate Similarity	NPC477918
0.8125	Intermediate Similarity	NPC169389
0.809	Intermediate Similarity	NPC41649
0.8077	Intermediate Similarity	NPC474755
0.8049	Intermediate Similarity	NPC125366
0.8	Intermediate Similarity	NPC471046
0.7901	Intermediate Similarity	NPC471151
0.7882	Intermediate Similarity	NPC471044
0.7882	Intermediate Similarity	NPC473336
0.7875	Intermediate Similarity	NPC477934
0.7857	Intermediate Similarity	NPC24556
0.7849	Intermediate Similarity	NPC267921
0.7831	Intermediate Similarity	NPC134227
0.7791	Intermediate Similarity	NPC473350
0.7778	Intermediate Similarity	NPC477933
0.7778	Intermediate Similarity	NPC476189
0.7778	Intermediate Similarity	NPC477932
0.775	Intermediate Similarity	NPC55508
0.7738	Intermediate Similarity	NPC472229
0.7738	Intermediate Similarity	NPC472230
0.7727	Intermediate Similarity	NPC56413
0.7722	Intermediate Similarity	NPC470243
0.7722	Intermediate Similarity	NPC469940
0.7711	Intermediate Similarity	NPC474754
0.7708	Intermediate Similarity	NPC88469
0.7703	Intermediate Similarity	NPC306750
0.7692	Intermediate Similarity	NPC295788
0.7674	Intermediate Similarity	NPC65133
0.7654	Intermediate Similarity	NPC132064
0.7654	Intermediate Similarity	NPC472311
0.764	Intermediate Similarity	NPC67653
0.764	Intermediate Similarity	NPC471459
0.764	Intermediate Similarity	NPC61688
0.7625	Intermediate Similarity	NPC109510
0.7619	Intermediate Similarity	NPC170038
0.7609	Intermediate Similarity	NPC287354
0.7609	Intermediate Similarity	NPC62407
0.7582	Intermediate Similarity	NPC472237
0.7582	Intermediate Similarity	NPC472238
0.7582	Intermediate Similarity	NPC161035
0.7582	Intermediate Similarity	NPC228700
0.7558	Intermediate Similarity	NPC472847
0.7558	Intermediate Similarity	NPC217559
0.7558	Intermediate Similarity	NPC292458
0.7558	Intermediate Similarity	NPC268578
0.7558	Intermediate Similarity	NPC15821
0.7553	Intermediate Similarity	NPC26270
0.7531	Intermediate Similarity	NPC477867
0.7531	Intermediate Similarity	NPC477930
0.7529	Intermediate Similarity	NPC58631
0.7528	Intermediate Similarity	NPC90676
0.7527	Intermediate Similarity	NPC116683
0.75	Intermediate Similarity	NPC477441
0.75	Intermediate Similarity	NPC470424
0.75	Intermediate Similarity	NPC206878
0.75	Intermediate Similarity	NPC92139
0.75	Intermediate Similarity	NPC118987
0.7471	Intermediate Similarity	NPC181871
0.7471	Intermediate Similarity	NPC477434
0.7471	Intermediate Similarity	NPC319909
0.7471	Intermediate Similarity	NPC9060
0.747	Intermediate Similarity	NPC143250
0.7449	Intermediate Similarity	NPC103172
0.7449	Intermediate Similarity	NPC164600
0.7447	Intermediate Similarity	NPC96839
0.7442	Intermediate Similarity	NPC102156
0.7442	Intermediate Similarity	NPC477935
0.7442	Intermediate Similarity	NPC148740
0.7442	Intermediate Similarity	NPC477936
0.7442	Intermediate Similarity	NPC61107
0.7442	Intermediate Similarity	NPC289486
0.7442	Intermediate Similarity	NPC242771
0.7442	Intermediate Similarity	NPC164289
0.7442	Intermediate Similarity	NPC311642
0.7442	Intermediate Similarity	NPC100366
0.7439	Intermediate Similarity	NPC179858
0.7416	Intermediate Similarity	NPC239938
0.7412	Intermediate Similarity	NPC472853
0.7407	Intermediate Similarity	NPC475230
0.7396	Intermediate Similarity	NPC39683
0.7396	Intermediate Similarity	NPC148279
0.7396	Intermediate Similarity	NPC178853
0.7391	Intermediate Similarity	NPC474379
0.7386	Intermediate Similarity	NPC477205
0.7386	Intermediate Similarity	NPC470223
0.7386	Intermediate Similarity	NPC474572
0.7381	Intermediate Similarity	NPC185465
0.7375	Intermediate Similarity	NPC477929
0.7374	Intermediate Similarity	NPC88833
0.7374	Intermediate Similarity	NPC96333
0.7363	Intermediate Similarity	NPC77756
0.7347	Intermediate Similarity	NPC244247
0.7347	Intermediate Similarity	NPC101842
0.7333	Intermediate Similarity	NPC477614
0.7333	Intermediate Similarity	NPC226491
0.7333	Intermediate Similarity	NPC221993
0.7333	Intermediate Similarity	NPC471221
0.732	Intermediate Similarity	NPC471254
0.732	Intermediate Similarity	NPC470172
0.7312	Intermediate Similarity	NPC224410
0.7312	Intermediate Similarity	NPC477495
0.7312	Intermediate Similarity	NPC100257
0.7312	Intermediate Similarity	NPC470423
0.7308	Intermediate Similarity	NPC268736
0.7308	Intermediate Similarity	NPC84562
0.7308	Intermediate Similarity	NPC477931
0.7303	Intermediate Similarity	NPC120395
0.7294	Intermediate Similarity	NPC201276
0.7294	Intermediate Similarity	NPC472310
0.7294	Intermediate Similarity	NPC477287
0.7294	Intermediate Similarity	NPC31302
0.7294	Intermediate Similarity	NPC245029
0.7294	Intermediate Similarity	NPC80891
0.7294	Intermediate Similarity	NPC320144
0.7284	Intermediate Similarity	NPC472309
0.7284	Intermediate Similarity	NPC473267
0.7284	Intermediate Similarity	NPC478227
0.7283	Intermediate Similarity	NPC52756
0.7283	Intermediate Similarity	NPC470230
0.7283	Intermediate Similarity	NPC216137
0.7273	Intermediate Similarity	NPC473299
0.7273	Intermediate Similarity	NPC237938
0.7273	Intermediate Similarity	NPC219535
0.7263	Intermediate Similarity	NPC253586
0.7263	Intermediate Similarity	NPC469810
0.7262	Intermediate Similarity	NPC474404
0.7262	Intermediate Similarity	NPC207010
0.7262	Intermediate Similarity	NPC317913
0.7253	Intermediate Similarity	NPC477440
0.7253	Intermediate Similarity	NPC472234
0.7253	Intermediate Similarity	NPC477443
0.7253	Intermediate Similarity	NPC472233
0.7253	Intermediate Similarity	NPC471043
0.725	Intermediate Similarity	NPC319671
0.725	Intermediate Similarity	NPC476734
0.725	Intermediate Similarity	NPC252032
0.725	Intermediate Similarity	NPC469941
0.725	Intermediate Similarity	NPC64466
0.7245	Intermediate Similarity	NPC471253
0.7245	Intermediate Similarity	NPC473406
0.7245	Intermediate Similarity	NPC96217
0.7234	Intermediate Similarity	NPC305808
0.7229	Intermediate Similarity	NPC179922
0.7216	Intermediate Similarity	NPC236585
0.7209	Intermediate Similarity	NPC60568
0.7209	Intermediate Similarity	NPC261616
0.72	Intermediate Similarity	NPC61071
0.7195	Intermediate Similarity	NPC474123
0.7188	Intermediate Similarity	NPC253995
0.7188	Intermediate Similarity	NPC471038
0.7188	Intermediate Similarity	NPC474793
0.7188	Intermediate Similarity	NPC271387
0.7188	Intermediate Similarity	NPC153792
0.7179	Intermediate Similarity	NPC157518
0.7176	Intermediate Similarity	NPC171426
0.7176	Intermediate Similarity	NPC199965
0.7176	Intermediate Similarity	NPC34046
0.7176	Intermediate Similarity	NPC476732
0.7176	Intermediate Similarity	NPC324700
0.7176	Intermediate Similarity	NPC224802
0.7176	Intermediate Similarity	NPC80089
0.7174	Intermediate Similarity	NPC477444
0.7174	Intermediate Similarity	NPC477433
0.7174	Intermediate Similarity	NPC477442
0.716	Intermediate Similarity	NPC477850
0.716	Intermediate Similarity	NPC476731
0.716	Intermediate Similarity	NPC108131
0.7159	Intermediate Similarity	NPC15091
0.7157	Intermediate Similarity	NPC49730
0.7157	Intermediate Similarity	NPC98069
0.7143	Intermediate Similarity	NPC33398
0.7143	Intermediate Similarity	NPC201607
0.7143	Intermediate Similarity	NPC236459
0.7143	Intermediate Similarity	NPC28227
0.7143	Intermediate Similarity	NPC473319
0.7143	Intermediate Similarity	NPC4209
0.7143	Intermediate Similarity	NPC131104
0.7143	Intermediate Similarity	NPC56777
0.7143	Intermediate Similarity	NPC3032
0.7128	Intermediate Similarity	NPC475118
0.7128	Intermediate Similarity	NPC247877
0.7128	Intermediate Similarity	NPC309127
0.7126	Intermediate Similarity	NPC329490
0.7126	Intermediate Similarity	NPC475951
0.7126	Intermediate Similarity	NPC232625
0.7126	Intermediate Similarity	NPC475743
0.7126	Intermediate Similarity	NPC328639
0.7113	Intermediate Similarity	NPC108371
0.7111	Intermediate Similarity	NPC302111
0.7111	Intermediate Similarity	NPC114378
0.7111	Intermediate Similarity	NPC103782

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 NPC1882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	3833
0.2-0.3	3340
0.3-0.4	961
0.4-0.5	239
0.5-0.6	263
0.6-0.7	66
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7875	Intermediate Similarity	NPD3702	Approved
0.7722	Intermediate Similarity	NPD5777	Approved
0.7308	Intermediate Similarity	NPD4224	Phase 2
0.7284	Intermediate Similarity	NPD6081	Approved
0.7262	Intermediate Similarity	NPD6116	Phase 1
0.7179	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6118	Approved
0.7176	Intermediate Similarity	NPD6115	Approved
0.7176	Intermediate Similarity	NPD6114	Approved
0.7176	Intermediate Similarity	NPD6697	Approved
0.7143	Intermediate Similarity	NPD6117	Approved
0.7108	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4789	Approved
0.6931	Remote Similarity	NPD6008	Approved
0.6867	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6399	Phase 3
0.6829	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3698	Phase 2
0.6829	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3703	Phase 2
0.6774	Remote Similarity	NPD6672	Approved
0.6774	Remote Similarity	NPD5737	Approved
0.6747	Remote Similarity	NPD4244	Approved
0.6747	Remote Similarity	NPD4245	Approved
0.6742	Remote Similarity	NPD1780	Approved
0.6742	Remote Similarity	NPD1779	Approved
0.6737	Remote Similarity	NPD8035	Phase 2
0.6737	Remote Similarity	NPD8034	Phase 2
0.6707	Remote Similarity	NPD5360	Phase 3
0.6707	Remote Similarity	NPD229	Approved
0.6707	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6903	Approved
0.6591	Remote Similarity	NPD4802	Phase 2
0.6591	Remote Similarity	NPD4238	Approved
0.6559	Remote Similarity	NPD7521	Approved
0.6559	Remote Similarity	NPD7334	Approved
0.6559	Remote Similarity	NPD5330	Approved
0.6559	Remote Similarity	NPD6409	Approved
0.6559	Remote Similarity	NPD6684	Approved
0.6559	Remote Similarity	NPD7146	Approved
0.6471	Remote Similarity	NPD4758	Discontinued
0.6458	Remote Similarity	NPD5207	Approved
0.6444	Remote Similarity	NPD6928	Phase 2
0.6429	Remote Similarity	NPD6001	Approved
0.6421	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6098	Approved
0.6354	Remote Similarity	NPD6673	Approved
0.6354	Remote Similarity	NPD6080	Approved
0.6354	Remote Similarity	NPD6904	Approved
0.6341	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5696	Approved
0.6321	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5208	Approved
0.6238	Remote Similarity	NPD6084	Phase 2
0.6238	Remote Similarity	NPD6083	Phase 2
0.6224	Remote Similarity	NPD5693	Phase 1
0.6222	Remote Similarity	NPD5364	Discontinued
0.6222	Remote Similarity	NPD3671	Phase 1
0.62	Remote Similarity	NPD5695	Phase 3
0.6168	Remote Similarity	NPD7320	Approved
0.6132	Remote Similarity	NPD6675	Approved
0.6132	Remote Similarity	NPD6402	Approved
0.6132	Remote Similarity	NPD7128	Approved
0.6132	Remote Similarity	NPD5739	Approved
0.6122	Remote Similarity	NPD5692	Phase 3
0.6111	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD6373	Approved
0.61	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7900	Approved
0.6095	Remote Similarity	NPD6052	Approved
0.6075	Remote Similarity	NPD5697	Approved
0.6075	Remote Similarity	NPD5701	Approved
0.6068	Remote Similarity	NPD7492	Approved
0.6064	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD3669	Approved
0.6064	Remote Similarity	NPD4788	Approved
0.6061	Remote Similarity	NPD5694	Approved
0.6061	Remote Similarity	NPD5281	Approved
0.6061	Remote Similarity	NPD6050	Approved
0.6061	Remote Similarity	NPD5284	Approved
0.6042	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6011	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6017	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD4786	Approved
0.5979	Remote Similarity	NPD3573	Approved
0.5966	Remote Similarity	NPD8293	Discontinued
0.5966	Remote Similarity	NPD7078	Approved
0.5963	Remote Similarity	NPD6013	Approved
0.5963	Remote Similarity	NPD6014	Approved
0.5963	Remote Similarity	NPD6012	Approved
0.5957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD3667	Approved
0.5948	Remote Similarity	NPD6016	Approved
0.5948	Remote Similarity	NPD6015	Approved
0.5926	Remote Similarity	NPD6412	Phase 2
0.5922	Remote Similarity	NPD7902	Approved
0.5917	Remote Similarity	NPD7736	Approved
0.5909	Remote Similarity	NPD6883	Approved
0.5909	Remote Similarity	NPD7102	Approved
0.5909	Remote Similarity	NPD7290	Approved
0.5897	Remote Similarity	NPD6370	Approved
0.5897	Remote Similarity	NPD5988	Approved
0.5897	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4632	Approved
0.5888	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5654	Approved
0.5876	Remote Similarity	NPD3618	Phase 1
0.587	Remote Similarity	NPD3617	Approved
0.5865	Remote Similarity	NPD7638	Approved
0.5862	Remote Similarity	NPD3726	Approved
0.5862	Remote Similarity	NPD3725	Approved
0.5859	Remote Similarity	NPD4753	Phase 2
0.5859	Remote Similarity	NPD5328	Approved
0.5856	Remote Similarity	NPD8130	Phase 1
0.5856	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6617	Approved
0.5856	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD6847	Approved
0.5842	Remote Similarity	NPD8171	Discontinued
0.5833	Remote Similarity	NPD3666	Approved
0.5833	Remote Similarity	NPD3665	Phase 1
0.5833	Remote Similarity	NPD3133	Approved
0.5825	Remote Similarity	NPD4697	Phase 3
0.5818	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7640	Approved
0.581	Remote Similarity	NPD7639	Approved
0.581	Remote Similarity	NPD8418	Phase 2
0.5804	Remote Similarity	NPD6882	Approved
0.5804	Remote Similarity	NPD8297	Approved
0.5789	Remote Similarity	NPD4221	Approved
0.5789	Remote Similarity	NPD4223	Phase 3
0.5789	Remote Similarity	NPD6940	Discontinued
0.5784	Remote Similarity	NPD5282	Discontinued
0.5784	Remote Similarity	NPD7748	Approved
0.578	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD1694	Approved
0.5769	Remote Similarity	NPD5959	Approved
0.5769	Remote Similarity	NPD4755	Approved
0.5752	Remote Similarity	NPD8133	Approved
0.5743	Remote Similarity	NPD6411	Approved
0.5743	Remote Similarity	NPD6079	Approved
0.5739	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7115	Discovery
0.5739	Remote Similarity	NPD6009	Approved
0.5738	Remote Similarity	NPD7319	Approved
0.5732	Remote Similarity	NPD3198	Approved
0.5728	Remote Similarity	NPD5210	Approved
0.5728	Remote Similarity	NPD7991	Discontinued
0.5728	Remote Similarity	NPD4629	Approved
0.5701	Remote Similarity	NPD7632	Discontinued
0.57	Remote Similarity	NPD6051	Approved
0.5686	Remote Similarity	NPD4202	Approved
0.5684	Remote Similarity	NPD4139	Approved
0.5684	Remote Similarity	NPD4692	Approved
0.5682	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6921	Approved
0.5678	Remote Similarity	NPD5983	Phase 2
0.5673	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5221	Approved
0.5673	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5222	Approved
0.567	Remote Similarity	NPD4197	Approved
0.566	Remote Similarity	NPD5285	Approved
0.566	Remote Similarity	NPD4696	Approved
0.566	Remote Similarity	NPD4700	Approved
0.566	Remote Similarity	NPD5286	Approved
0.5656	Remote Similarity	NPD6033	Approved
0.5652	Remote Similarity	NPD6274	Approved
0.5641	Remote Similarity	NPD7518	Approved
0.5641	Remote Similarity	NPD7519	Approved
0.5641	Remote Similarity	NPD7517	Approved
0.5636	Remote Similarity	NPD6614	Approved
0.5625	Remote Similarity	NPD4634	Approved
0.5625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7507	Approved
0.5619	Remote Similarity	NPD5173	Approved
0.5618	Remote Similarity	NPD2687	Approved
0.5618	Remote Similarity	NPD2254	Approved
0.5618	Remote Similarity	NPD2686	Approved
0.5618	Remote Similarity	NPD4747	Approved
0.5612	Remote Similarity	NPD5329	Approved
0.5607	Remote Similarity	NPD5223	Approved
0.5603	Remote Similarity	NPD6317	Approved
0.56	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.56	Remote Similarity	NPD344	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