NPASS Compound

Structure

NPC472971 OpenBabel07101719522D 23 25 0 0 1 0 0 0 0 0999 V2000 5.1369 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6369 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 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 1.7321 -2.0000 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 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 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6369 -1.8660 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 4.1369 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 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 5.6369 -0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -2.7601 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 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 6 0 0 0 13 18 1 0 0 0 0 14 20 1 6 0 0 0 15 19 1 0 0 0 0 15 20 1 6 0 0 0 16 19 1 0 0 0 0 16 21 1 6 0 0 0 17 22 2 0 0 0 0 18 23 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	3.211
LogD:	2.079
LogS:	-2.467
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.767
Synthetic Accessibility Score:	4.557
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.506
MDCK Permeability:	2.0353185391286388e-05
Pgp-inhibitor:	0.069
Pgp-substrate:	0.885
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.472
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.897
Plasma Protein Binding (PPB):	56.16279602050781%
Volume Distribution (VD):	1.686
Pgp-substrate:	47.185340881347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	10.489
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.204
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.317
Carcinogencity:	0.435
Eye Corrosion:	0.681
Eye Irritation:	0.512
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC472971

Natural Product ID:	NPC472971
*Common Name:**	BRENCONTRXLLMU-BFAUHDMXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BRENCONTRXLLMU-BFAUHDMXSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-11(2)17(22)13-10-14-12(18(13)23)6-7-15-19(3,4)16(21)8-9-20(14,15)5/h6,11,13-16,18,21,23H,7-10H2,1-5H3/t13-,14-,15-,16-,18-,20+/m1/s1
SMILES:	O=C([C@H]1C[C@@H]2C(=CC[C@H]3[C@@]2(C)CC[C@H](C3(C)C)O)[C@H]1O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594335
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

*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

Activity Type	# Activity
NON-MOLECULAR	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	>	100000.0	nM	PMID[572751]

☑ 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 NPC472971 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	154
0.1-0.2	1102
0.2-0.3	4727
0.3-0.4	12996
0.4-0.5	10271
0.5-0.6	6594
0.6-0.7	4971
0.7-0.8	1697
0.8-0.85	156
0.85-0.9	27
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472970
0.8966	High Similarity	NPC328313
0.8953	High Similarity	NPC469994
0.8916	High Similarity	NPC104120
0.8916	High Similarity	NPC157895
0.8916	High Similarity	NPC148685
0.8864	High Similarity	NPC309603
0.8864	High Similarity	NPC2983
0.8864	High Similarity	NPC473999
0.8837	High Similarity	NPC474083
0.8837	High Similarity	NPC471224
0.8778	High Similarity	NPC477520
0.8778	High Similarity	NPC69454
0.8764	High Similarity	NPC69622
0.8764	High Similarity	NPC48010
0.875	High Similarity	NPC471724
0.8736	High Similarity	NPC470955
0.8721	High Similarity	NPC82902
0.8667	High Similarity	NPC233116
0.8667	High Similarity	NPC475806
0.8667	High Similarity	NPC63748
0.8667	High Similarity	NPC473998
0.8636	High Similarity	NPC317590
0.8621	High Similarity	NPC179006
0.8621	High Similarity	NPC474853
0.8621	High Similarity	NPC474218
0.8617	High Similarity	NPC154072
0.8587	High Similarity	NPC259286
0.8587	High Similarity	NPC271195
0.8571	High Similarity	NPC472942
0.8556	High Similarity	NPC320026
0.8539	High Similarity	NPC53911
0.8539	High Similarity	NPC471722
0.8523	High Similarity	NPC94755
0.8523	High Similarity	NPC194417
0.8523	High Similarity	NPC72133
0.8511	High Similarity	NPC48647
0.8506	High Similarity	NPC59453
0.8506	High Similarity	NPC221758
0.8506	High Similarity	NPC165064
0.8495	Intermediate Similarity	NPC249954
0.8488	Intermediate Similarity	NPC46881
0.8478	Intermediate Similarity	NPC469406
0.8478	Intermediate Similarity	NPC111015
0.8478	Intermediate Similarity	NPC8993
0.8444	Intermediate Similarity	NPC472489
0.8444	Intermediate Similarity	NPC472475
0.8444	Intermediate Similarity	NPC472983
0.8444	Intermediate Similarity	NPC76879
0.8444	Intermediate Similarity	NPC472477
0.8444	Intermediate Similarity	NPC275740
0.8444	Intermediate Similarity	NPC86319
0.8438	Intermediate Similarity	NPC477915
0.8438	Intermediate Similarity	NPC473424
0.8427	Intermediate Similarity	NPC159046
0.8427	Intermediate Similarity	NPC233836
0.8427	Intermediate Similarity	NPC475740
0.8427	Intermediate Similarity	NPC472481
0.8427	Intermediate Similarity	NPC474684
0.8427	Intermediate Similarity	NPC472482
0.8427	Intermediate Similarity	NPC187376
0.8427	Intermediate Similarity	NPC472484
0.8427	Intermediate Similarity	NPC142361
0.8421	Intermediate Similarity	NPC110149
0.8409	Intermediate Similarity	NPC470574
0.8391	Intermediate Similarity	NPC105173
0.8391	Intermediate Similarity	NPC278648
0.8391	Intermediate Similarity	NPC476082
0.8387	Intermediate Similarity	NPC472932
0.8387	Intermediate Similarity	NPC472485
0.837	Intermediate Similarity	NPC472930
0.837	Intermediate Similarity	NPC470375
0.837	Intermediate Similarity	NPC470376
0.8353	Intermediate Similarity	NPC308038
0.8352	Intermediate Similarity	NPC469400
0.8352	Intermediate Similarity	NPC191684
0.8333	Intermediate Similarity	NPC474854
0.8333	Intermediate Similarity	NPC143767
0.8333	Intermediate Similarity	NPC328539
0.8333	Intermediate Similarity	NPC193360
0.8333	Intermediate Similarity	NPC74995
0.8333	Intermediate Similarity	NPC131470
0.8316	Intermediate Similarity	NPC186810
0.8316	Intermediate Similarity	NPC103051
0.8315	Intermediate Similarity	NPC145879
0.8315	Intermediate Similarity	NPC28252
0.8315	Intermediate Similarity	NPC51014
0.8315	Intermediate Similarity	NPC472985
0.8315	Intermediate Similarity	NPC198761
0.8315	Intermediate Similarity	NPC31564
0.8315	Intermediate Similarity	NPC476043
0.8315	Intermediate Similarity	NPC472494
0.8315	Intermediate Similarity	NPC473226
0.8315	Intermediate Similarity	NPC472491
0.8315	Intermediate Similarity	NPC474733
0.8315	Intermediate Similarity	NPC472986
0.8315	Intermediate Similarity	NPC55309
0.8315	Intermediate Similarity	NPC474732
0.8315	Intermediate Similarity	NPC474778
0.8295	Intermediate Similarity	NPC214043
0.8295	Intermediate Similarity	NPC473246
0.8295	Intermediate Similarity	NPC58841
0.8295	Intermediate Similarity	NPC321187
0.8295	Intermediate Similarity	NPC161423
0.8295	Intermediate Similarity	NPC227064
0.8295	Intermediate Similarity	NPC85774
0.8295	Intermediate Similarity	NPC329043
0.828	Intermediate Similarity	NPC299100
0.828	Intermediate Similarity	NPC292793
0.828	Intermediate Similarity	NPC474690
0.8276	Intermediate Similarity	NPC110780
0.8276	Intermediate Similarity	NPC93590
0.8276	Intermediate Similarity	NPC151519
0.8276	Intermediate Similarity	NPC48362
0.8265	Intermediate Similarity	NPC204833
0.8265	Intermediate Similarity	NPC209502
0.8261	Intermediate Similarity	NPC272746
0.8261	Intermediate Similarity	NPC297265
0.8261	Intermediate Similarity	NPC23434
0.8256	Intermediate Similarity	NPC172013
0.8242	Intermediate Similarity	NPC474704
0.8242	Intermediate Similarity	NPC77168
0.8242	Intermediate Similarity	NPC31985
0.8242	Intermediate Similarity	NPC1015
0.8242	Intermediate Similarity	NPC472973
0.8242	Intermediate Similarity	NPC69627
0.8242	Intermediate Similarity	NPC84271
0.8242	Intermediate Similarity	NPC102414
0.8242	Intermediate Similarity	NPC477943
0.8242	Intermediate Similarity	NPC474245
0.8242	Intermediate Similarity	NPC475921
0.8242	Intermediate Similarity	NPC32830
0.8242	Intermediate Similarity	NPC214387
0.8235	Intermediate Similarity	NPC297996
0.8229	Intermediate Similarity	NPC477521
0.8222	Intermediate Similarity	NPC141292
0.8222	Intermediate Similarity	NPC96496
0.8222	Intermediate Similarity	NPC472495
0.8222	Intermediate Similarity	NPC58063
0.8222	Intermediate Similarity	NPC472497
0.8211	Intermediate Similarity	NPC107243
0.8211	Intermediate Similarity	NPC320306
0.8211	Intermediate Similarity	NPC475894
0.8211	Intermediate Similarity	NPC190554
0.8202	Intermediate Similarity	NPC202868
0.8202	Intermediate Similarity	NPC133954
0.8202	Intermediate Similarity	NPC292553
0.8202	Intermediate Similarity	NPC274724
0.8191	Intermediate Similarity	NPC45324
0.8191	Intermediate Similarity	NPC162001
0.8191	Intermediate Similarity	NPC263347
0.8191	Intermediate Similarity	NPC180950
0.8191	Intermediate Similarity	NPC222845
0.8182	Intermediate Similarity	NPC302607
0.8182	Intermediate Similarity	NPC202167
0.8182	Intermediate Similarity	NPC48733
0.8182	Intermediate Similarity	NPC85829
0.8182	Intermediate Similarity	NPC319077
0.8182	Intermediate Similarity	NPC257353
0.8182	Intermediate Similarity	NPC97202
0.8182	Intermediate Similarity	NPC49958
0.8182	Intermediate Similarity	NPC214264
0.8182	Intermediate Similarity	NPC260268
0.8182	Intermediate Similarity	NPC476027
0.8182	Intermediate Similarity	NPC471036
0.8182	Intermediate Similarity	NPC150531
0.8182	Intermediate Similarity	NPC166607
0.8182	Intermediate Similarity	NPC474748
0.8182	Intermediate Similarity	NPC291320
0.8182	Intermediate Similarity	NPC296945
0.8182	Intermediate Similarity	NPC171137
0.8182	Intermediate Similarity	NPC152695
0.8182	Intermediate Similarity	NPC50692
0.8182	Intermediate Similarity	NPC149047
0.8172	Intermediate Similarity	NPC243866
0.8172	Intermediate Similarity	NPC474736
0.8172	Intermediate Similarity	NPC109305
0.8172	Intermediate Similarity	NPC475255
0.8163	Intermediate Similarity	NPC26478
0.8161	Intermediate Similarity	NPC473420
0.8161	Intermediate Similarity	NPC14151
0.8152	Intermediate Similarity	NPC472476
0.8152	Intermediate Similarity	NPC183283
0.8152	Intermediate Similarity	NPC126993
0.8152	Intermediate Similarity	NPC477149
0.8152	Intermediate Similarity	NPC171441
0.8152	Intermediate Similarity	NPC477147
0.8152	Intermediate Similarity	NPC85173
0.8144	Intermediate Similarity	NPC282524
0.8144	Intermediate Similarity	NPC472924
0.814	Intermediate Similarity	NPC30986
0.814	Intermediate Similarity	NPC7232
0.814	Intermediate Similarity	NPC152061
0.814	Intermediate Similarity	NPC281138
0.814	Intermediate Similarity	NPC209430
0.814	Intermediate Similarity	NPC1319
0.8132	Intermediate Similarity	NPC310752
0.8132	Intermediate Similarity	NPC292491
0.8132	Intermediate Similarity	NPC242864
0.8132	Intermediate Similarity	NPC472483

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 NPC472971 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1501
0.2-0.3	4016
0.3-0.4	2419
0.4-0.5	595
0.5-0.6	182
0.6-0.7	168
0.7-0.8	119
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8506	High Similarity	NPD4786	Approved
0.8444	Intermediate Similarity	NPD5328	Approved
0.837	Intermediate Similarity	NPD4202	Approved
0.8315	Intermediate Similarity	NPD3618	Phase 1
0.8295	Intermediate Similarity	NPD3133	Approved
0.8295	Intermediate Similarity	NPD3665	Phase 1
0.8295	Intermediate Similarity	NPD3666	Approved
0.8276	Intermediate Similarity	NPD3667	Approved
0.8261	Intermediate Similarity	NPD6079	Approved
0.8061	Intermediate Similarity	NPD5211	Phase 2
0.8021	Intermediate Similarity	NPD4755	Approved
0.79	Intermediate Similarity	NPD5141	Approved
0.7865	Intermediate Similarity	NPD4223	Phase 3
0.7865	Intermediate Similarity	NPD4221	Approved
0.7857	Intermediate Similarity	NPD5285	Approved
0.7857	Intermediate Similarity	NPD5286	Approved
0.7857	Intermediate Similarity	NPD4700	Approved
0.7857	Intermediate Similarity	NPD4696	Approved
0.7849	Intermediate Similarity	NPD4753	Phase 2
0.7802	Intermediate Similarity	NPD5329	Approved
0.7778	Intermediate Similarity	NPD5223	Approved
0.7732	Intermediate Similarity	NPD4697	Phase 3
0.7732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD5222	Approved
0.7732	Intermediate Similarity	NPD5221	Approved
0.7717	Intermediate Similarity	NPD5279	Phase 3
0.7717	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5225	Approved
0.77	Intermediate Similarity	NPD4633	Approved
0.77	Intermediate Similarity	NPD5226	Approved
0.77	Intermediate Similarity	NPD5224	Approved
0.7692	Intermediate Similarity	NPD4197	Approved
0.7684	Intermediate Similarity	NPD7515	Phase 2
0.7653	Intermediate Similarity	NPD5173	Approved
0.7647	Intermediate Similarity	NPD6675	Approved
0.7647	Intermediate Similarity	NPD5739	Approved
0.7647	Intermediate Similarity	NPD6402	Approved
0.7647	Intermediate Similarity	NPD7128	Approved
0.7624	Intermediate Similarity	NPD4754	Approved
0.7624	Intermediate Similarity	NPD5175	Approved
0.7624	Intermediate Similarity	NPD5174	Approved
0.7609	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD6399	Phase 3
0.7586	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4788	Approved
0.7527	Intermediate Similarity	NPD4694	Approved
0.7527	Intermediate Similarity	NPD6684	Approved
0.7527	Intermediate Similarity	NPD5690	Phase 2
0.7527	Intermediate Similarity	NPD7334	Approved
0.7527	Intermediate Similarity	NPD7521	Approved
0.7527	Intermediate Similarity	NPD6409	Approved
0.7527	Intermediate Similarity	NPD5205	Approved
0.7527	Intermediate Similarity	NPD4689	Approved
0.7527	Intermediate Similarity	NPD4138	Approved
0.7527	Intermediate Similarity	NPD5330	Approved
0.7527	Intermediate Similarity	NPD7146	Approved
0.7527	Intermediate Similarity	NPD4690	Approved
0.7527	Intermediate Similarity	NPD5280	Approved
0.7527	Intermediate Similarity	NPD4688	Approved
0.7527	Intermediate Similarity	NPD4693	Phase 3
0.7524	Intermediate Similarity	NPD4634	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD4768	Approved
0.7476	Intermediate Similarity	NPD4767	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7473	Intermediate Similarity	NPD4269	Approved
0.7473	Intermediate Similarity	NPD4270	Approved
0.7471	Intermediate Similarity	NPD6942	Approved
0.7471	Intermediate Similarity	NPD7339	Approved
0.7449	Intermediate Similarity	NPD4629	Approved
0.7449	Intermediate Similarity	NPD5210	Approved
0.7447	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7525	Registered
0.7431	Intermediate Similarity	NPD7115	Discovery
0.7429	Intermediate Similarity	NPD6372	Approved
0.7429	Intermediate Similarity	NPD6373	Approved
0.7416	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5701	Approved
0.7404	Intermediate Similarity	NPD5697	Approved
0.74	Intermediate Similarity	NPD7638	Approved
0.7368	Intermediate Similarity	NPD6903	Approved
0.7368	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4692	Approved
0.7363	Intermediate Similarity	NPD4139	Approved
0.7358	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD7102	Approved
0.7358	Intermediate Similarity	NPD7290	Approved
0.7347	Intermediate Similarity	NPD7748	Approved
0.734	Intermediate Similarity	NPD4519	Discontinued
0.734	Intermediate Similarity	NPD4623	Approved
0.7333	Intermediate Similarity	NPD6011	Approved
0.7333	Intermediate Similarity	NPD4729	Approved
0.7333	Intermediate Similarity	NPD5128	Approved
0.7333	Intermediate Similarity	NPD4730	Approved
0.729	Intermediate Similarity	NPD6869	Approved
0.729	Intermediate Similarity	NPD6847	Approved
0.729	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6650	Approved
0.729	Intermediate Similarity	NPD6617	Approved
0.729	Intermediate Similarity	NPD6649	Approved
0.729	Intermediate Similarity	NPD8130	Phase 1
0.7273	Intermediate Similarity	NPD5695	Phase 3
0.7264	Intermediate Similarity	NPD6012	Approved
0.7264	Intermediate Similarity	NPD6014	Approved
0.7264	Intermediate Similarity	NPD6013	Approved
0.7253	Intermediate Similarity	NPD4252	Approved
0.7234	Intermediate Similarity	NPD5363	Approved
0.7222	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6882	Approved
0.7216	Intermediate Similarity	NPD5785	Approved
0.7204	Intermediate Similarity	NPD5362	Discontinued
0.7196	Intermediate Similarity	NPD5249	Phase 3
0.7196	Intermediate Similarity	NPD5248	Approved
0.7196	Intermediate Similarity	NPD5247	Approved
0.7196	Intermediate Similarity	NPD5250	Approved
0.7196	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5135	Approved
0.7196	Intermediate Similarity	NPD5251	Approved
0.7196	Intermediate Similarity	NPD5169	Approved
0.7158	Intermediate Similarity	NPD6098	Approved
0.7158	Intermediate Similarity	NPD5786	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.713	Intermediate Similarity	NPD5217	Approved
0.713	Intermediate Similarity	NPD5216	Approved
0.713	Intermediate Similarity	NPD5127	Approved
0.713	Intermediate Similarity	NPD5215	Approved
0.7129	Intermediate Similarity	NPD7902	Approved
0.7126	Intermediate Similarity	NPD4243	Approved
0.7126	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6059	Approved
0.708	Intermediate Similarity	NPD6054	Approved
0.7079	Intermediate Similarity	NPD8264	Approved
0.7071	Intermediate Similarity	NPD5778	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7065	Intermediate Similarity	NPD4748	Discontinued
0.7059	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD5696	Approved
0.7041	Intermediate Similarity	NPD4096	Approved
0.7033	Intermediate Similarity	NPD3617	Approved
0.7011	Intermediate Similarity	NPD4244	Approved
0.7011	Intermediate Similarity	NPD4245	Approved
0.701	Intermediate Similarity	NPD5737	Approved
0.701	Intermediate Similarity	NPD6672	Approved
0.7009	Intermediate Similarity	NPD5168	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.6989	Remote Similarity	NPD5369	Approved
0.697	Remote Similarity	NPD6411	Approved
0.697	Remote Similarity	NPD8034	Phase 2
0.697	Remote Similarity	NPD8035	Phase 2
0.697	Remote Similarity	NPD7637	Suspended
0.6966	Remote Similarity	NPD4784	Approved
0.6966	Remote Similarity	NPD6926	Approved
0.6966	Remote Similarity	NPD6924	Approved
0.6966	Remote Similarity	NPD4785	Approved
0.6957	Remote Similarity	NPD6929	Approved
0.6957	Remote Similarity	NPD6370	Approved
0.6939	Remote Similarity	NPD6673	Approved
0.6939	Remote Similarity	NPD6904	Approved
0.6939	Remote Similarity	NPD6080	Approved
0.6937	Remote Similarity	NPD5167	Approved
0.693	Remote Similarity	NPD6319	Approved
0.6916	Remote Similarity	NPD6412	Phase 2
0.6903	Remote Similarity	NPD6335	Approved
0.69	Remote Similarity	NPD5133	Approved
0.6897	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3698	Phase 2
0.6882	Remote Similarity	NPD6930	Phase 2
0.6882	Remote Similarity	NPD6931	Approved
0.6882	Remote Similarity	NPD4695	Discontinued
0.6875	Remote Similarity	NPD1696	Phase 3
0.6875	Remote Similarity	NPD6274	Approved
0.6875	Remote Similarity	NPD1694	Approved
0.687	Remote Similarity	NPD6016	Approved
0.687	Remote Similarity	NPD6015	Approved
0.6857	Remote Similarity	NPD7632	Discontinued
0.6842	Remote Similarity	NPD7100	Approved
0.6842	Remote Similarity	NPD5331	Approved
0.6842	Remote Similarity	NPD7101	Approved
0.6842	Remote Similarity	NPD5332	Approved
0.6838	Remote Similarity	NPD7492	Approved
0.6837	Remote Similarity	NPD4518	Approved
0.6837	Remote Similarity	NPD5208	Approved
0.6832	Remote Similarity	NPD6001	Approved
0.6832	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7900	Approved
0.6824	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD4747	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