NPASS Compound

Structure

NPC289140 OpenBabel07101719512D 32 36 0 0 1 0 0 0 0 0999 V2000 -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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4568 -0.1910 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4458 -0.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4513 -0.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2647 -2.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6879 -2.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8525 -1.3136 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 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 5.2812 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2702 -2.0181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6824 -2.8271 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8635 -1.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.8471 -1.4181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0892 -3.7406 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 16 1 0 0 0 0 5 29 1 0 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 28 1 0 0 0 0 10 15 1 0 0 0 0 10 26 1 0 0 0 0 11 18 1 0 0 0 0 11 24 1 0 0 0 0 12 21 1 0 0 0 0 12 23 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 29 1 0 0 0 0 15 1 1 1 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 17 3 1 6 0 0 0 18 30 1 6 0 0 0 19 17 1 6 0 0 0 20 7 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 13 1 1 0 0 0 22 23 1 0 0 0 0 23 28 1 6 0 0 0 24 25 1 0 0 0 0 24 28 1 6 0 0 0 25 31 1 6 0 0 0 26 27 1 0 0 0 0 26 32 1 6 0 0 0 27 17 1 6 0 0 0 27 29 1 0 0 0 0 28 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	445.36
Volume:	484.793
LogP:	4.333
LogD:	4.322
LogS:	-4.251
# Rotatable Bonds:	2
TPSA:	63.93
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	5.305
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.914
MDCK Permeability:	2.0286899598431773e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.081

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	88.34026336669922%
Volume Distribution (VD):	1.392
Pgp-substrate:	3.492875337600708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.17
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.823

ADMET: Excretion

Clearance (CL):	8.966
Half-life (T1/2):	0.457

ADMET: Toxicity

hERG Blockers:	0.804
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.79
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.914
Carcinogencity:	0.067
Eye Corrosion:	0.036
Eye Irritation:	0.045
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC289140

Natural Product ID:	NPC289140
*Common Name:**	Puqienine A
IUPAC Name:	(3S,4aS,5R,6aR,6bS,9R,11aS,11bR)-9-[(1R)-1-[(2R,3R,5R)-3-hydroxy-1,5-dimethylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1,2,3,4,4a,5,6,6a,6b,7,8,9,11,11a-tetradecahydrobenzo[a]fluorene-3,5-diol
Synonyms:
Standard InCHIKey:	GRTDQRFJWHCECY-SAYBQXENSA-N
Standard InCHI:	InChI=1S/C28H47NO3/c1-15-10-26(32)27(29(5)14-15)17(3)19-6-7-20-21(16(19)2)12-23-22(20)13-25(31)24-11-18(30)8-9-28(23,24)4/h15,17-20,22-27,30-32H,6-14H2,1-5H3/t15-,17-,18+,19+,20-,22+,23+,24-,25-,26-,27-,28-/m1/s1
SMILES:	C[C@@H]1C[C@H]([C@@H]([C@H](C)[C@H]2CC[C@@H]3C(=C2C)C[C@H]2[C@H]3C[C@H]([C@H]3C[C@H](CC[C@]23C)O)O)N(C)C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500390
PubChem CID:	11351298
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000195] Piperidines

*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
NPO20194	Fritillaria puqiensis	Species	Liliaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[15730259]
NPO20194	Fritillaria puqiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20194	Fritillaria puqiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20194	Fritillaria puqiensis	Species	Liliaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.0	n.a.	PMID[570138]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.0	n.a.	PMID[570138]

☑ 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 NPC289140 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	96
0.1-0.2	1001
0.2-0.3	12415
0.3-0.4	14820
0.4-0.5	6823
0.5-0.6	5717
0.6-0.7	1669
0.7-0.8	146
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8878	High Similarity	NPC475239
0.8515	High Similarity	NPC46981
0.8381	Intermediate Similarity	NPC478137
0.8367	Intermediate Similarity	NPC91604
0.8351	Intermediate Similarity	NPC476903
0.83	Intermediate Similarity	NPC176012
0.8265	Intermediate Similarity	NPC474164
0.8137	Intermediate Similarity	NPC212874
0.79	Intermediate Similarity	NPC140300
0.7872	Intermediate Similarity	NPC75810
0.7864	Intermediate Similarity	NPC241879
0.7767	Intermediate Similarity	NPC50815
0.7767	Intermediate Similarity	NPC471083
0.7736	Intermediate Similarity	NPC159367
0.7727	Intermediate Similarity	NPC28280
0.7727	Intermediate Similarity	NPC304646
0.7664	Intermediate Similarity	NPC147835
0.7664	Intermediate Similarity	NPC95920
0.7664	Intermediate Similarity	NPC85001
0.7664	Intermediate Similarity	NPC253645
0.7642	Intermediate Similarity	NPC25340
0.7634	Intermediate Similarity	NPC109533
0.7596	Intermediate Similarity	NPC247060
0.7593	Intermediate Similarity	NPC287764
0.7549	Intermediate Similarity	NPC240650
0.7478	Intermediate Similarity	NPC478138
0.7476	Intermediate Similarity	NPC220111
0.7475	Intermediate Similarity	NPC312637
0.7455	Intermediate Similarity	NPC56796
0.7455	Intermediate Similarity	NPC476498
0.7426	Intermediate Similarity	NPC243985
0.7426	Intermediate Similarity	NPC280710
0.7383	Intermediate Similarity	NPC55462
0.7383	Intermediate Similarity	NPC86906
0.7358	Intermediate Similarity	NPC474583
0.7353	Intermediate Similarity	NPC311164
0.7353	Intermediate Similarity	NPC272732
0.7333	Intermediate Similarity	NPC201373
0.7327	Intermediate Similarity	NPC93027
0.7321	Intermediate Similarity	NPC476499
0.7312	Intermediate Similarity	NPC244385
0.7312	Intermediate Similarity	NPC138621
0.7312	Intermediate Similarity	NPC167037
0.7312	Intermediate Similarity	NPC6978
0.7283	Intermediate Similarity	NPC73875
0.7283	Intermediate Similarity	NPC189883
0.7273	Intermediate Similarity	NPC472359
0.7238	Intermediate Similarity	NPC135799
0.7234	Intermediate Similarity	NPC273410
0.7234	Intermediate Similarity	NPC80530
0.7234	Intermediate Similarity	NPC1319
0.7204	Intermediate Similarity	NPC214570
0.7196	Intermediate Similarity	NPC293299
0.7196	Intermediate Similarity	NPC45365
0.719	Intermediate Similarity	NPC478139
0.7188	Intermediate Similarity	NPC20853
0.7174	Intermediate Similarity	NPC322353
0.7174	Intermediate Similarity	NPC121744
0.7174	Intermediate Similarity	NPC471723
0.7174	Intermediate Similarity	NPC118508
0.7174	Intermediate Similarity	NPC257347
0.7174	Intermediate Similarity	NPC141071
0.7158	Intermediate Similarity	NPC236237
0.7158	Intermediate Similarity	NPC102253
0.7158	Intermediate Similarity	NPC236112
0.7158	Intermediate Similarity	NPC322313
0.713	Intermediate Similarity	NPC470596
0.7129	Intermediate Similarity	NPC84171
0.7128	Intermediate Similarity	NPC285761
0.7128	Intermediate Similarity	NPC275910
0.7097	Intermediate Similarity	NPC202642
0.7097	Intermediate Similarity	NPC300324
0.7097	Intermediate Similarity	NPC14112
0.7097	Intermediate Similarity	NPC107059
0.7097	Intermediate Similarity	NPC237460
0.7097	Intermediate Similarity	NPC321381
0.7097	Intermediate Similarity	NPC321016
0.7097	Intermediate Similarity	NPC129165
0.7097	Intermediate Similarity	NPC134330
0.7097	Intermediate Similarity	NPC240604
0.7097	Intermediate Similarity	NPC46160
0.7097	Intermediate Similarity	NPC86305
0.7083	Intermediate Similarity	NPC474531
0.7083	Intermediate Similarity	NPC317654
0.7083	Intermediate Similarity	NPC96010
0.7075	Intermediate Similarity	NPC275686
0.7071	Intermediate Similarity	NPC24277
0.7064	Intermediate Similarity	NPC477292
0.7059	Intermediate Similarity	NPC296686
0.7054	Intermediate Similarity	NPC79238
0.7053	Intermediate Similarity	NPC209430
0.7053	Intermediate Similarity	NPC155924
0.7053	Intermediate Similarity	NPC30986
0.7041	Intermediate Similarity	NPC478102
0.7041	Intermediate Similarity	NPC124172
0.7041	Intermediate Similarity	NPC209802
0.7021	Intermediate Similarity	NPC198968
0.7021	Intermediate Similarity	NPC155986
0.7021	Intermediate Similarity	NPC318495
0.7019	Intermediate Similarity	NPC155985
0.7019	Intermediate Similarity	NPC174117
0.701	Intermediate Similarity	NPC248886
0.701	Intermediate Similarity	NPC30166
0.701	Intermediate Similarity	NPC470049
0.7009	Intermediate Similarity	NPC118275
0.7	Intermediate Similarity	NPC169375
0.7	Intermediate Similarity	NPC265275
0.7	Intermediate Similarity	NPC48886
0.7	Intermediate Similarity	NPC94881
0.6989	Remote Similarity	NPC288035
0.6989	Remote Similarity	NPC3403
0.6989	Remote Similarity	NPC162742
0.6989	Remote Similarity	NPC104387
0.6989	Remote Similarity	NPC240235
0.6989	Remote Similarity	NPC136188
0.6989	Remote Similarity	NPC231256
0.6989	Remote Similarity	NPC28657
0.6989	Remote Similarity	NPC212879
0.6989	Remote Similarity	NPC22105
0.6989	Remote Similarity	NPC230301
0.6989	Remote Similarity	NPC178383
0.6989	Remote Similarity	NPC285893
0.6989	Remote Similarity	NPC134847
0.6989	Remote Similarity	NPC304309
0.6979	Remote Similarity	NPC13554
0.6979	Remote Similarity	NPC22403
0.697	Remote Similarity	NPC16350
0.697	Remote Similarity	NPC308041
0.6957	Remote Similarity	NPC474140
0.6949	Remote Similarity	NPC476504
0.6947	Remote Similarity	NPC474216
0.6947	Remote Similarity	NPC85346
0.6947	Remote Similarity	NPC87604
0.6947	Remote Similarity	NPC205455
0.6947	Remote Similarity	NPC473943
0.6947	Remote Similarity	NPC300499
0.6947	Remote Similarity	NPC65897
0.6947	Remote Similarity	NPC186191
0.6947	Remote Similarity	NPC477522
0.6947	Remote Similarity	NPC302041
0.6939	Remote Similarity	NPC246956
0.6939	Remote Similarity	NPC207013
0.6939	Remote Similarity	NPC110778
0.6939	Remote Similarity	NPC477818
0.6937	Remote Similarity	NPC470595
0.6931	Remote Similarity	NPC470542
0.6917	Remote Similarity	NPC476503
0.6915	Remote Similarity	NPC106432
0.6915	Remote Similarity	NPC470362
0.6915	Remote Similarity	NPC93662
0.6915	Remote Similarity	NPC78067
0.6915	Remote Similarity	NPC113733
0.6915	Remote Similarity	NPC278091
0.6907	Remote Similarity	NPC470383
0.6907	Remote Similarity	NPC6707
0.6903	Remote Similarity	NPC474459
0.6887	Remote Similarity	NPC292819
0.6882	Remote Similarity	NPC25511
0.6882	Remote Similarity	NPC62657
0.6882	Remote Similarity	NPC192638
0.6882	Remote Similarity	NPC469533
0.6882	Remote Similarity	NPC100334
0.6882	Remote Similarity	NPC469593
0.6882	Remote Similarity	NPC469534
0.6881	Remote Similarity	NPC90538
0.6875	Remote Similarity	NPC109546
0.6875	Remote Similarity	NPC28862
0.6875	Remote Similarity	NPC274895
0.6875	Remote Similarity	NPC84694
0.6875	Remote Similarity	NPC47982
0.6875	Remote Similarity	NPC143182
0.6875	Remote Similarity	NPC328714
0.6875	Remote Similarity	NPC81306
0.6869	Remote Similarity	NPC470077
0.6863	Remote Similarity	NPC105495
0.6863	Remote Similarity	NPC101886
0.6863	Remote Similarity	NPC138974
0.6855	Remote Similarity	NPC40488
0.6848	Remote Similarity	NPC111234
0.6842	Remote Similarity	NPC101475
0.6842	Remote Similarity	NPC202540
0.6842	Remote Similarity	NPC40394
0.6842	Remote Similarity	NPC248830
0.6842	Remote Similarity	NPC472805
0.6842	Remote Similarity	NPC119355
0.6842	Remote Similarity	NPC474452
0.6842	Remote Similarity	NPC90979
0.6842	Remote Similarity	NPC34177
0.6842	Remote Similarity	NPC34019
0.6842	Remote Similarity	NPC157996
0.6842	Remote Similarity	NPC212241
0.6837	Remote Similarity	NPC5985
0.6837	Remote Similarity	NPC101462
0.6837	Remote Similarity	NPC202389
0.6837	Remote Similarity	NPC296701
0.6837	Remote Similarity	NPC218616
0.6837	Remote Similarity	NPC7988
0.6837	Remote Similarity	NPC1272
0.6837	Remote Similarity	NPC201852
0.6837	Remote Similarity	NPC49964

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 NPC289140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	599
0.2-0.3	3992
0.3-0.4	3162
0.4-0.5	892
0.5-0.6	308
0.6-0.7	108
0.7-0.8	1
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
0.7158	Intermediate Similarity	NPD7525	Registered
0.6989	Remote Similarity	NPD7339	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6909	Remote Similarity	NPD6920	Discontinued
0.6842	Remote Similarity	NPD7336	Phase 2
0.6842	Remote Similarity	NPD7335	Phase 2
0.6842	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6415	Discontinued
0.6737	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7645	Phase 2
0.6698	Remote Similarity	NPD7991	Discontinued
0.6696	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6633	Remote Similarity	NPD4748	Discontinued
0.6607	Remote Similarity	NPD7333	Discontinued
0.6574	Remote Similarity	NPD7919	Phase 3
0.6574	Remote Similarity	NPD7920	Phase 3
0.6538	Remote Similarity	NPD5328	Approved
0.6535	Remote Similarity	NPD4786	Approved
0.6535	Remote Similarity	NPD8449	Approved
0.6525	Remote Similarity	NPD7754	Approved
0.6525	Remote Similarity	NPD7755	Approved
0.6514	Remote Similarity	NPD8088	Phase 1
0.6484	Remote Similarity	NPD8450	Suspended
0.6481	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6079	Approved
0.6408	Remote Similarity	NPD3618	Phase 1
0.6356	Remote Similarity	NPD8298	Phase 2
0.6355	Remote Similarity	NPD4202	Approved
0.6354	Remote Similarity	NPD6926	Approved
0.6354	Remote Similarity	NPD6924	Approved
0.6337	Remote Similarity	NPD3667	Approved
0.6316	Remote Similarity	NPD4243	Approved
0.6311	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5771	Approved
0.6283	Remote Similarity	NPD7911	Approved
0.6283	Remote Similarity	NPD7987	Approved
0.6283	Remote Similarity	NPD7912	Approved
0.6283	Remote Similarity	NPD7986	Approved
0.625	Remote Similarity	NPD8308	Discontinued
0.623	Remote Similarity	NPD7522	Discontinued
0.6224	Remote Similarity	NPD6933	Approved
0.619	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4784	Approved
0.6186	Remote Similarity	NPD4785	Approved
0.6174	Remote Similarity	NPD8040	Discontinued
0.6146	Remote Similarity	NPD7152	Approved
0.6146	Remote Similarity	NPD7151	Approved
0.6146	Remote Similarity	NPD7150	Approved
0.6139	Remote Similarity	NPD7509	Discontinued
0.6134	Remote Similarity	NPD8077	Approved
0.6134	Remote Similarity	NPD8078	Approved
0.6126	Remote Similarity	NPD4755	Approved
0.6121	Remote Similarity	NPD7989	Approved
0.6121	Remote Similarity	NPD7990	Approved
0.6106	Remote Similarity	NPD4159	Approved
0.6105	Remote Similarity	NPD6923	Approved
0.6105	Remote Similarity	NPD6922	Approved
0.6105	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3666	Approved
0.6058	Remote Similarity	NPD3665	Phase 1
0.6058	Remote Similarity	NPD3133	Approved
0.6055	Remote Similarity	NPD6399	Phase 3
0.6042	Remote Similarity	NPD7143	Approved
0.6042	Remote Similarity	NPD7144	Approved
0.604	Remote Similarity	NPD6929	Approved
0.6036	Remote Similarity	NPD5221	Approved
0.6036	Remote Similarity	NPD5222	Approved
0.6036	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD4697	Phase 3
0.6032	Remote Similarity	NPD7122	Discontinued
0.6018	Remote Similarity	NPD8418	Phase 2
0.6018	Remote Similarity	NPD4700	Approved
0.6018	Remote Similarity	NPD5285	Approved
0.6018	Remote Similarity	NPD4696	Approved
0.6018	Remote Similarity	NPD5286	Approved
0.5982	Remote Similarity	NPD5173	Approved
0.5981	Remote Similarity	NPD4722	Approved
0.5981	Remote Similarity	NPD4723	Approved
0.598	Remote Similarity	NPD6930	Phase 2
0.598	Remote Similarity	NPD6931	Approved
0.5968	Remote Similarity	NPD7518	Approved
0.5968	Remote Similarity	NPD7517	Approved
0.5968	Remote Similarity	NPD7519	Approved
0.5965	Remote Similarity	NPD5223	Approved
0.5963	Remote Similarity	NPD8034	Phase 2
0.5963	Remote Similarity	NPD8035	Phase 2
0.5963	Remote Similarity	NPD7515	Phase 2
0.596	Remote Similarity	NPD4190	Phase 3
0.596	Remote Similarity	NPD5275	Approved
0.5913	Remote Similarity	NPD4633	Approved
0.5913	Remote Similarity	NPD5226	Approved
0.5913	Remote Similarity	NPD5224	Approved
0.5913	Remote Similarity	NPD5211	Phase 2
0.5913	Remote Similarity	NPD5225	Approved
0.5905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7128	Approved
0.5897	Remote Similarity	NPD6402	Approved
0.5897	Remote Similarity	NPD6675	Approved
0.5897	Remote Similarity	NPD5739	Approved
0.5882	Remote Similarity	NPD4195	Approved
0.5876	Remote Similarity	NPD4787	Phase 1
0.5872	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6700	Approved
0.5862	Remote Similarity	NPD4754	Approved
0.5862	Remote Similarity	NPD5174	Approved
0.5862	Remote Similarity	NPD5175	Approved
0.5842	Remote Similarity	NPD5776	Phase 2
0.5842	Remote Similarity	NPD6925	Approved
0.5842	Remote Similarity	NPD6932	Approved
0.5842	Remote Similarity	NPD6116	Phase 1
0.5833	Remote Similarity	NPD6705	Phase 1
0.5827	Remote Similarity	NPD7725	Approved
0.5825	Remote Similarity	NPD6928	Phase 2
0.5818	Remote Similarity	NPD6702	Approved
0.5818	Remote Similarity	NPD6703	Approved
0.5816	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5141	Approved
0.581	Remote Similarity	NPD6695	Phase 3
0.5798	Remote Similarity	NPD7320	Approved
0.5798	Remote Similarity	NPD8174	Phase 2
0.5798	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6881	Approved
0.5794	Remote Similarity	NPD5279	Phase 3
0.5789	Remote Similarity	NPD7638	Approved
0.5789	Remote Similarity	NPD5290	Discontinued
0.5784	Remote Similarity	NPD7145	Approved
0.5784	Remote Similarity	NPD3617	Approved
0.578	Remote Similarity	NPD4753	Phase 2
0.5763	Remote Similarity	NPD4767	Approved
0.5763	Remote Similarity	NPD4768	Approved
0.5755	Remote Similarity	NPD3668	Phase 3
0.575	Remote Similarity	NPD6372	Approved
0.575	Remote Similarity	NPD6373	Approved
0.5743	Remote Similarity	NPD6117	Approved
0.5739	Remote Similarity	NPD7639	Approved
0.5739	Remote Similarity	NPD7640	Approved
0.5728	Remote Similarity	NPD6683	Phase 2
0.5714	Remote Similarity	NPD4221	Approved
0.5714	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD5701	Approved
0.5714	Remote Similarity	NPD4223	Phase 3
0.5702	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD7102	Approved
0.5701	Remote Similarity	NPD6893	Approved
0.5701	Remote Similarity	NPD5329	Approved
0.57	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD8144	Approved
0.5686	Remote Similarity	NPD8143	Approved
0.5673	Remote Similarity	NPD7514	Phase 3
0.5667	Remote Similarity	NPD6011	Approved
0.5667	Remote Similarity	NPD4729	Approved
0.5667	Remote Similarity	NPD5128	Approved
0.5667	Remote Similarity	NPD4730	Approved
0.566	Remote Similarity	NPD4788	Approved
0.5656	Remote Similarity	NPD6869	Approved
0.5656	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6847	Approved
0.5656	Remote Similarity	NPD6617	Approved
0.5656	Remote Similarity	NPD6649	Approved
0.5656	Remote Similarity	NPD8130	Phase 1
0.5656	Remote Similarity	NPD6650	Approved
0.5648	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD8264	Approved
0.5641	Remote Similarity	NPD4719	Phase 2
0.5641	Remote Similarity	NPD7632	Discontinued
0.5631	Remote Similarity	NPD6114	Approved
0.5631	Remote Similarity	NPD6115	Approved
0.5631	Remote Similarity	NPD6697	Approved
0.5631	Remote Similarity	NPD6118	Approved
0.5631	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6012	Approved
0.562	Remote Similarity	NPD6014	Approved
0.562	Remote Similarity	NPD6013	Approved
0.5619	Remote Similarity	NPD4692	Approved
0.5619	Remote Similarity	NPD6902	Approved
0.5619	Remote Similarity	NPD4139	Approved
0.5612	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8297	Approved
0.561	Remote Similarity	NPD6882	Approved
0.5607	Remote Similarity	NPD4197	Approved
0.5606	Remote Similarity	NPD8336	Approved
0.5606	Remote Similarity	NPD8337	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