NPASS Compound

Structure

NPC472977 OpenBabel07101719522D 24 26 0 0 1 0 0 0 0 0999 V2000 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 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 2.5981 -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 3.4641 -1.0000 0.0000 C 0 0 0 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 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 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 4.3301 -2.5000 0.0000 C 0 0 2 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 -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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 0.1305 0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 1 0 0 0 14 21 2 0 0 0 0 15 18 1 0 0 0 0 15 19 1 1 0 0 0 16 18 1 0 0 0 0 16 22 1 1 0 0 0 17 20 1 6 0 0 0 17 23 1 0 0 0 0 19 5 1 1 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	358.695
LogP:	2.707
LogD:	2.383
LogS:	-3.996
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.74
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:	-4.712
MDCK Permeability:	2.7358411898603663e-05
Pgp-inhibitor:	0.919
Pgp-substrate:	0.739
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	47.08464050292969%
Volume Distribution (VD):	0.965
Pgp-substrate:	49.0817985534668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.205
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	5.179
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.473
Carcinogencity:	0.242
Eye Corrosion:	0.015
Eye Irritation:	0.867
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC472977

Natural Product ID:	NPC472977
*Common Name:**	NHJLCDALTNPYBE-FNYOEWHISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NHJLCDALTNPYBE-FNYOEWHISA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-11(2)20(24)10-12-13(8-17(20)23)19(5)7-6-16(22)18(3,4)15(19)9-14(12)21/h10-11,13,15-17,22-24H,6-9H2,1-5H3/t13-,15-,16-,17-,19+,20+/m1/s1
SMILES:	CC(C)C1(C=C2C(CC1O)C3(CCC(C(C3CC2=O)(C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594341
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32900	chloranthus sessilifolius	Species	Chloranthaceae	Eukaryota	Whole plants	Fengqi Mountains, Sichuan Province, China	2012-Aug	PMID[26126961]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37700.0	nM	PMID[523704]
NPT27	Others	Unspecified		Activity	=	98.4	%	PMID[523704]

☑ 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 NPC472977 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	194
0.1-0.2	1163
0.2-0.3	3976
0.3-0.4	8254
0.4-0.5	13829
0.5-0.6	7288
0.6-0.7	5298
0.7-0.8	2428
0.8-0.85	222
0.85-0.9	36
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472976
0.9545	High Similarity	NPC472978
0.954	High Similarity	NPC472973
0.913	High Similarity	NPC471463
0.9111	High Similarity	NPC472975
0.9053	High Similarity	NPC473424
0.9022	High Similarity	NPC473170
0.8989	High Similarity	NPC158778
0.8977	High Similarity	NPC472974
0.8966	High Similarity	NPC476412
0.8913	High Similarity	NPC470957
0.8913	High Similarity	NPC470958
0.8913	High Similarity	NPC196227
0.8901	High Similarity	NPC116726
0.8854	High Similarity	NPC477915
0.8804	High Similarity	NPC109305
0.8776	High Similarity	NPC149047
0.8764	High Similarity	NPC472986
0.8764	High Similarity	NPC472985
0.8723	High Similarity	NPC117133
0.8723	High Similarity	NPC249954
0.87	High Similarity	NPC214644
0.8687	High Similarity	NPC475060
0.8687	High Similarity	NPC220229
0.8681	High Similarity	NPC472983
0.8673	High Similarity	NPC209502
0.8673	High Similarity	NPC204833
0.8667	High Similarity	NPC472324
0.8636	High Similarity	NPC251475
0.8636	High Similarity	NPC169941
0.8632	High Similarity	NPC474938
0.8632	High Similarity	NPC474785
0.8632	High Similarity	NPC161147
0.8617	High Similarity	NPC259286
0.8617	High Similarity	NPC53565
0.8602	High Similarity	NPC69454
0.8602	High Similarity	NPC474736
0.86	High Similarity	NPC217201
0.8587	High Similarity	NPC48010
0.8587	High Similarity	NPC134321
0.8587	High Similarity	NPC472325
0.8586	High Similarity	NPC150531
0.8586	High Similarity	NPC214264
0.8586	High Similarity	NPC48733
0.8586	High Similarity	NPC260268
0.8586	High Similarity	NPC171137
0.8586	High Similarity	NPC152695
0.8586	High Similarity	NPC85829
0.8586	High Similarity	NPC476027
0.8586	High Similarity	NPC319077
0.8586	High Similarity	NPC296945
0.8586	High Similarity	NPC97202
0.8586	High Similarity	NPC50692
0.8586	High Similarity	NPC302607
0.8586	High Similarity	NPC202167
0.8586	High Similarity	NPC49958
0.8571	High Similarity	NPC104560
0.8542	High Similarity	NPC478056
0.8539	High Similarity	NPC40687
0.8523	High Similarity	NPC212083
0.8515	High Similarity	NPC11710
0.8511	High Similarity	NPC299100
0.8511	High Similarity	NPC8993
0.8511	High Similarity	NPC473162
0.85	High Similarity	NPC83744
0.85	High Similarity	NPC477916
0.8495	Intermediate Similarity	NPC473998
0.8495	Intermediate Similarity	NPC63748
0.8495	Intermediate Similarity	NPC475806
0.8495	Intermediate Similarity	NPC155304
0.8478	Intermediate Similarity	NPC32830
0.8478	Intermediate Similarity	NPC473999
0.8478	Intermediate Similarity	NPC229871
0.8478	Intermediate Similarity	NPC309603
0.8478	Intermediate Similarity	NPC469319
0.8478	Intermediate Similarity	NPC473100
0.8469	Intermediate Similarity	NPC136289
0.8444	Intermediate Similarity	NPC470574
0.8444	Intermediate Similarity	NPC476426
0.8438	Intermediate Similarity	NPC253826
0.8427	Intermediate Similarity	NPC66764
0.8427	Intermediate Similarity	NPC64600
0.8427	Intermediate Similarity	NPC105173
0.8427	Intermediate Similarity	NPC110150
0.8421	Intermediate Similarity	NPC272617
0.8421	Intermediate Similarity	NPC271195
0.8421	Intermediate Similarity	NPC134067
0.8421	Intermediate Similarity	NPC180950
0.8421	Intermediate Similarity	NPC266899
0.8416	Intermediate Similarity	NPC329417
0.8416	Intermediate Similarity	NPC65941
0.8404	Intermediate Similarity	NPC472930
0.84	Intermediate Similarity	NPC323834
0.8391	Intermediate Similarity	NPC308038
0.8387	Intermediate Similarity	NPC473099
0.8387	Intermediate Similarity	NPC230332
0.8387	Intermediate Similarity	NPC128672
0.8384	Intermediate Similarity	NPC311612
0.837	Intermediate Similarity	NPC328539
0.837	Intermediate Similarity	NPC206060
0.837	Intermediate Similarity	NPC474925
0.837	Intermediate Similarity	NPC48107
0.8367	Intermediate Similarity	NPC81530
0.8352	Intermediate Similarity	NPC179591
0.8352	Intermediate Similarity	NPC470955
0.8333	Intermediate Similarity	NPC61369
0.8333	Intermediate Similarity	NPC227132
0.8333	Intermediate Similarity	NPC469545
0.8333	Intermediate Similarity	NPC473158
0.8333	Intermediate Similarity	NPC5532
0.8317	Intermediate Similarity	NPC185
0.8316	Intermediate Similarity	NPC23170
0.8316	Intermediate Similarity	NPC103527
0.8316	Intermediate Similarity	NPC474690
0.8316	Intermediate Similarity	NPC473172
0.8316	Intermediate Similarity	NPC471207
0.8315	Intermediate Similarity	NPC93590
0.8315	Intermediate Similarity	NPC48362
0.83	Intermediate Similarity	NPC118911
0.8298	Intermediate Similarity	NPC73457
0.8298	Intermediate Similarity	NPC185936
0.8298	Intermediate Similarity	NPC168027
0.8298	Intermediate Similarity	NPC99380
0.8295	Intermediate Similarity	NPC2482
0.8283	Intermediate Similarity	NPC87351
0.828	Intermediate Similarity	NPC1015
0.828	Intermediate Similarity	NPC86319
0.828	Intermediate Similarity	NPC119416
0.828	Intermediate Similarity	NPC31985
0.828	Intermediate Similarity	NPC275740
0.828	Intermediate Similarity	NPC77263
0.828	Intermediate Similarity	NPC123912
0.828	Intermediate Similarity	NPC250592
0.8276	Intermediate Similarity	NPC475994
0.8276	Intermediate Similarity	NPC62336
0.8265	Intermediate Similarity	NPC198880
0.8265	Intermediate Similarity	NPC316964
0.8265	Intermediate Similarity	NPC154072
0.8261	Intermediate Similarity	NPC471792
0.8261	Intermediate Similarity	NPC475740
0.8261	Intermediate Similarity	NPC477926
0.8261	Intermediate Similarity	NPC476409
0.8261	Intermediate Similarity	NPC298904
0.8252	Intermediate Similarity	NPC76084
0.8247	Intermediate Similarity	NPC474343
0.8247	Intermediate Similarity	NPC470522
0.8247	Intermediate Similarity	NPC135685
0.8247	Intermediate Similarity	NPC474977
0.8247	Intermediate Similarity	NPC170131
0.8247	Intermediate Similarity	NPC254496
0.8242	Intermediate Similarity	NPC197823
0.8242	Intermediate Similarity	NPC79573
0.8229	Intermediate Similarity	NPC318282
0.8229	Intermediate Similarity	NPC174948
0.8229	Intermediate Similarity	NPC469995
0.8229	Intermediate Similarity	NPC472932
0.8229	Intermediate Similarity	NPC200702
0.8229	Intermediate Similarity	NPC139570
0.8229	Intermediate Similarity	NPC173875
0.8218	Intermediate Similarity	NPC478052
0.8211	Intermediate Similarity	NPC476416
0.8202	Intermediate Similarity	NPC473217
0.82	Intermediate Similarity	NPC90177
0.82	Intermediate Similarity	NPC264048
0.82	Intermediate Similarity	NPC475050
0.82	Intermediate Similarity	NPC249187
0.82	Intermediate Similarity	NPC95899
0.82	Intermediate Similarity	NPC478057
0.82	Intermediate Similarity	NPC247957
0.8191	Intermediate Similarity	NPC85173
0.819	Intermediate Similarity	NPC73300
0.819	Intermediate Similarity	NPC108721
0.8182	Intermediate Similarity	NPC476897
0.8182	Intermediate Similarity	NPC470184
0.8182	Intermediate Similarity	NPC163372
0.8182	Intermediate Similarity	NPC302537
0.8182	Intermediate Similarity	NPC281138
0.8182	Intermediate Similarity	NPC115862
0.8182	Intermediate Similarity	NPC170394
0.8182	Intermediate Similarity	NPC472637
0.8172	Intermediate Similarity	NPC471793
0.8172	Intermediate Similarity	NPC471791
0.8172	Intermediate Similarity	NPC131470
0.8172	Intermediate Similarity	NPC471722
0.8172	Intermediate Similarity	NPC472802
0.8172	Intermediate Similarity	NPC143767
0.8163	Intermediate Similarity	NPC471717
0.8163	Intermediate Similarity	NPC114274
0.8163	Intermediate Similarity	NPC197386
0.8163	Intermediate Similarity	NPC103051
0.8155	Intermediate Similarity	NPC87335
0.8152	Intermediate Similarity	NPC82979
0.8152	Intermediate Similarity	NPC475069
0.8152	Intermediate Similarity	NPC145879
0.8152	Intermediate Similarity	NPC322159
0.8152	Intermediate Similarity	NPC474778
0.8152	Intermediate Similarity	NPC474733
0.8152	Intermediate Similarity	NPC175145
0.8152	Intermediate Similarity	NPC73038
0.8152	Intermediate Similarity	NPC474732

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 NPC472977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1508
0.2-0.3	3611
0.3-0.4	2490
0.4-0.5	862
0.5-0.6	222
0.6-0.7	169
0.7-0.8	98
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8495	Intermediate Similarity	NPD6079	Approved
0.8478	Intermediate Similarity	NPD5328	Approved
0.8283	Intermediate Similarity	NPD5211	Phase 2
0.8152	Intermediate Similarity	NPD3618	Phase 1
0.8144	Intermediate Similarity	NPD5222	Approved
0.8144	Intermediate Similarity	NPD5221	Approved
0.8144	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD5141	Approved
0.8105	Intermediate Similarity	NPD7515	Phase 2
0.8081	Intermediate Similarity	NPD4696	Approved
0.8081	Intermediate Similarity	NPD5286	Approved
0.8081	Intermediate Similarity	NPD5285	Approved
0.8061	Intermediate Similarity	NPD5173	Approved
0.8061	Intermediate Similarity	NPD4755	Approved
0.8	Intermediate Similarity	NPD5223	Approved
0.7959	Intermediate Similarity	NPD4697	Phase 3
0.7935	Intermediate Similarity	NPD4786	Approved
0.7921	Intermediate Similarity	NPD4633	Approved
0.7921	Intermediate Similarity	NPD5224	Approved
0.7921	Intermediate Similarity	NPD5226	Approved
0.7921	Intermediate Similarity	NPD5225	Approved
0.7912	Intermediate Similarity	NPD3667	Approved
0.79	Intermediate Similarity	NPD4700	Approved
0.7889	Intermediate Similarity	NPD4695	Discontinued
0.7843	Intermediate Similarity	NPD5175	Approved
0.7843	Intermediate Similarity	NPD5174	Approved
0.7835	Intermediate Similarity	NPD4202	Approved
0.7798	Intermediate Similarity	NPD7115	Discovery
0.7755	Intermediate Similarity	NPD7748	Approved
0.7742	Intermediate Similarity	NPD3133	Approved
0.7742	Intermediate Similarity	NPD3665	Phase 1
0.7742	Intermediate Similarity	NPD3666	Approved
0.7736	Intermediate Similarity	NPD4634	Approved
0.7714	Intermediate Similarity	NPD6899	Approved
0.7714	Intermediate Similarity	NPD6881	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.767	Intermediate Similarity	NPD4754	Approved
0.7624	Intermediate Similarity	NPD4225	Approved
0.7619	Intermediate Similarity	NPD5697	Approved
0.7593	Intermediate Similarity	NPD8297	Approved
0.7579	Intermediate Similarity	NPD4623	Approved
0.7579	Intermediate Similarity	NPD4519	Discontinued
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6883	Approved
0.757	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD7290	Approved
0.7547	Intermediate Similarity	NPD4729	Approved
0.7547	Intermediate Similarity	NPD5128	Approved
0.7547	Intermediate Similarity	NPD7320	Approved
0.7547	Intermediate Similarity	NPD4730	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7526	Intermediate Similarity	NPD4753	Phase 2
0.7525	Intermediate Similarity	NPD7902	Approved
0.7524	Intermediate Similarity	NPD4768	Approved
0.7524	Intermediate Similarity	NPD4767	Approved
0.7523	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7453	Intermediate Similarity	NPD5701	Approved
0.7431	Intermediate Similarity	NPD6882	Approved
0.7407	Intermediate Similarity	NPD5249	Phase 3
0.7407	Intermediate Similarity	NPD5247	Approved
0.7407	Intermediate Similarity	NPD5250	Approved
0.7407	Intermediate Similarity	NPD5135	Approved
0.7407	Intermediate Similarity	NPD5251	Approved
0.7407	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5169	Approved
0.7407	Intermediate Similarity	NPD5248	Approved
0.7396	Intermediate Similarity	NPD5279	Phase 3
0.7383	Intermediate Similarity	NPD5168	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD3668	Phase 3
0.734	Intermediate Similarity	NPD4221	Approved
0.734	Intermediate Similarity	NPD4223	Phase 3
0.7339	Intermediate Similarity	NPD5217	Approved
0.7339	Intermediate Similarity	NPD5216	Approved
0.7339	Intermediate Similarity	NPD5215	Approved
0.7339	Intermediate Similarity	NPD5127	Approved
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4629	Approved
0.7327	Intermediate Similarity	NPD5210	Approved
0.73	Intermediate Similarity	NPD6399	Phase 3
0.7292	Intermediate Similarity	NPD1696	Phase 3
0.7292	Intermediate Similarity	NPD5329	Approved
0.7282	Intermediate Similarity	NPD7638	Approved
0.7228	Intermediate Similarity	NPD7900	Approved
0.7228	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6411	Approved
0.7188	Intermediate Similarity	NPD4197	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7168	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD5167	Approved
0.713	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD6054	Approved
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.7128	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7525	Registered
0.7105	Intermediate Similarity	NPD6335	Approved
0.7083	Intermediate Similarity	NPD4788	Approved
0.708	Intermediate Similarity	NPD6274	Approved
0.708	Intermediate Similarity	NPD6868	Approved
0.7064	Intermediate Similarity	NPD6686	Approved
0.7043	Intermediate Similarity	NPD7101	Approved
0.7043	Intermediate Similarity	NPD7100	Approved
0.7041	Intermediate Similarity	NPD5205	Approved
0.7041	Intermediate Similarity	NPD4138	Approved
0.7041	Intermediate Similarity	NPD4693	Phase 3
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD4689	Approved
0.7041	Intermediate Similarity	NPD4688	Approved
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD4690	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.7041	Intermediate Similarity	NPD5690	Phase 2
0.7037	Intermediate Similarity	NPD6008	Approved
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7018	Intermediate Similarity	NPD6317	Approved
0.7011	Intermediate Similarity	NPD7331	Phase 2
0.7009	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6059	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6412	Phase 2
0.6957	Remote Similarity	NPD6942	Approved
0.6957	Remote Similarity	NPD8264	Approved
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD7339	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6949	Remote Similarity	NPD7604	Phase 2
0.6939	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD6015	Approved
0.6915	Remote Similarity	NPD3617	Approved
0.69	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6903	Approved
0.69	Remote Similarity	NPD5737	Approved
0.69	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD7341	Phase 2
0.6891	Remote Similarity	NPD7492	Approved
0.6882	Remote Similarity	NPD6933	Approved
0.6882	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5280	Approved
0.6869	Remote Similarity	NPD4694	Approved
0.6864	Remote Similarity	NPD5988	Approved
0.6842	Remote Similarity	NPD4195	Approved
0.6833	Remote Similarity	NPD6336	Discontinued
0.6833	Remote Similarity	NPD7507	Approved
0.6833	Remote Similarity	NPD6616	Approved
0.6827	Remote Similarity	NPD5695	Phase 3
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8328	Phase 3
0.68	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5696	Approved
0.678	Remote Similarity	NPD6909	Approved
0.678	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6908	Approved
0.6777	Remote Similarity	NPD7078	Approved
0.6768	Remote Similarity	NPD5363	Approved
0.6768	Remote Similarity	NPD1694	Approved
0.6765	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD7614	Phase 1
0.6759	Remote Similarity	NPD7632	Discontinued
0.6757	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7736	Approved
0.6703	Remote Similarity	NPD4691	Approved
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD8293	Discontinued
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)

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