NPASS Compound

Structure

CID123019 OpenBabel06191715482D 31 36 0 0 1 0 0 0 0 0999 V2000 -5.7155 2.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8146 1.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8649 1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8862 -2.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4451 -1.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9400 -2.1136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0579 -0.5740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8240 -1.4275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6486 -0.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6494 1.9034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8248 1.4276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8248 -1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2971 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9513 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5528 -1.2446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6480 -0.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4734 0.4753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6488 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1118 -0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1211 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4737 1.4272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6477 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1214 1.4267 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9455 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8246 0.4757 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5524 0.2947 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9658 -0.0132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3866 2.6721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2976 1.9029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 20 2 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 27 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 26 1 1 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 22 11 1 1 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 28 1 0 0 0 0 24 25 1 1 0 0 0 24 31 1 0 0 0 0 25 30 1 0 0 0 0 26 27 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	419.25
Volume:	445.758
LogP:	4.641
LogD:	3.224
LogS:	-4.069
# Rotatable Bonds:	1
TPSA:	62.32
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	4.685
Fsp3:	0.593
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:	-4.951
MDCK Permeability:	2.7140275051351637e-05
Pgp-inhibitor:	0.841
Pgp-substrate:	0.64
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.865
Plasma Protein Binding (PPB):	94.96245574951172%
Volume Distribution (VD):	0.854
Pgp-substrate:	2.512193202972412%

ADMET: Metabolism

CYP1A2-inhibitor:	0.246
CYP1A2-substrate:	0.611
CYP2C19-inhibitor:	0.337
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.641
CYP2C9-substrate:	0.258
CYP2D6-inhibitor:	0.24
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.798

ADMET: Excretion

Clearance (CL):	7.357
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.534
AMES Toxicity:	0.221
Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.759
Carcinogencity:	0.847
Eye Corrosion:	0.007
Eye Irritation:	0.017
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC123019

Natural Product ID:	NPC123019
*Common Name:**	Dehydroxypaxilline
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GYSZYWSJZCKCBD-LXGUAGHKSA-N
Standard InCHI:	InChI=1S/C27H33NO3/c1-25(2,30)24-21(29)14-18-19-10-9-15-13-17-16-7-5-6-8-20(16)28-23(17)27(15,4)26(19,3)12-11-22(18)31-24/h5-8,14-15,19,22,24,28,30H,9-13H2,1-4H3/t15-,19-,22-,24-,26-,27+/m0/s1
SMILES:	O=C1C=C2[C@@H](O[C@@H]1C(O)(C)C)CC[C@]1([C@H]2CC[C@@H]2[C@]1(C)c1[nH]c3c(c1C2)cccc3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408948
PubChem CID:	14166134
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO32542	penicillium camemberti oucmdz-1492	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23886345]
NPO40587	Penicillium sp. (strain ZO-R1-1)	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117519]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7340	Grewia microcos	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9916	Gymnosporia wallichiana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11943	Streptomyces albogriseolus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO120	Tecoma stans	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	17100.0	nM	PMID[484585]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	>	150000.0	nM	PMID[484584]

☑ 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 NPC123019 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	313
0.1-0.2	1412
0.2-0.3	3562
0.3-0.4	16344
0.4-0.5	16075
0.5-0.6	3242
0.6-0.7	1538
0.7-0.8	154
0.8-0.85	27
0.85-0.9	19
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC235900
0.9421	High Similarity	NPC471284
0.933	High Similarity	NPC34271
0.9323	High Similarity	NPC96131
0.9082	High Similarity	NPC61813
0.8895	High Similarity	NPC165201
0.875	High Similarity	NPC119700
0.8656	High Similarity	NPC206967
0.8626	High Similarity	NPC198339
0.8622	High Similarity	NPC475165
0.8608	High Similarity	NPC18661
0.8592	High Similarity	NPC282033
0.8579	High Similarity	NPC250129
0.8571	High Similarity	NPC6093
0.8495	Intermediate Similarity	NPC99428
0.8453	Intermediate Similarity	NPC97525
0.8446	Intermediate Similarity	NPC475151
0.8429	Intermediate Similarity	NPC231342
0.84	Intermediate Similarity	NPC473547
0.8384	Intermediate Similarity	NPC284102
0.8358	Intermediate Similarity	NPC97388
0.8325	Intermediate Similarity	NPC187456
0.8309	Intermediate Similarity	NPC79107
0.8309	Intermediate Similarity	NPC475424
0.828	Intermediate Similarity	NPC302191
0.8247	Intermediate Similarity	NPC473747
0.8233	Intermediate Similarity	NPC94541
0.8233	Intermediate Similarity	NPC470843
0.8088	Intermediate Similarity	NPC160527
0.8088	Intermediate Similarity	NPC473650
0.7989	Intermediate Similarity	NPC154293
0.785	Intermediate Similarity	NPC473806
0.785	Intermediate Similarity	NPC471634
0.7847	Intermediate Similarity	NPC242446
0.7847	Intermediate Similarity	NPC475476
0.783	Intermediate Similarity	NPC235885
0.7817	Intermediate Similarity	NPC181502
0.7817	Intermediate Similarity	NPC85066
0.775	Intermediate Similarity	NPC32200
0.7707	Intermediate Similarity	NPC258062
0.7707	Intermediate Similarity	NPC127677
0.7703	Intermediate Similarity	NPC203614
0.7703	Intermediate Similarity	NPC204491
0.7664	Intermediate Similarity	NPC141428
0.7659	Intermediate Similarity	NPC46225
0.7659	Intermediate Similarity	NPC225821
0.7656	Intermediate Similarity	NPC300688
0.7653	Intermediate Similarity	NPC46413
0.7606	Intermediate Similarity	NPC2395
0.7604	Intermediate Similarity	NPC270009
0.76	Intermediate Similarity	NPC205403
0.7598	Intermediate Similarity	NPC98715
0.7593	Intermediate Similarity	NPC57690
0.7577	Intermediate Similarity	NPC472444
0.7552	Intermediate Similarity	NPC151939
0.7535	Intermediate Similarity	NPC147446
0.7526	Intermediate Similarity	NPC126492
0.75	Intermediate Similarity	NPC471458
0.75	Intermediate Similarity	NPC476319
0.7489	Intermediate Similarity	NPC290529
0.7487	Intermediate Similarity	NPC34508
0.7477	Intermediate Similarity	NPC470874
0.7476	Intermediate Similarity	NPC87856
0.7476	Intermediate Similarity	NPC151976
0.7476	Intermediate Similarity	NPC477043
0.7465	Intermediate Similarity	NPC267926
0.7453	Intermediate Similarity	NPC132211
0.7452	Intermediate Similarity	NPC470280
0.745	Intermediate Similarity	NPC67551
0.7433	Intermediate Similarity	NPC473320
0.7427	Intermediate Similarity	NPC477135
0.7426	Intermediate Similarity	NPC11445
0.7423	Intermediate Similarity	NPC472443
0.7418	Intermediate Similarity	NPC249428
0.7415	Intermediate Similarity	NPC300183
0.7404	Intermediate Similarity	NPC474905
0.7387	Intermediate Similarity	NPC61435
0.7376	Intermediate Similarity	NPC195239
0.7376	Intermediate Similarity	NPC157828
0.7373	Intermediate Similarity	NPC266192
0.7366	Intermediate Similarity	NPC313985
0.7366	Intermediate Similarity	NPC49196
0.7366	Intermediate Similarity	NPC195461
0.7366	Intermediate Similarity	NPC81654
0.7366	Intermediate Similarity	NPC249150
0.7366	Intermediate Similarity	NPC79129
0.7363	Intermediate Similarity	NPC47190
0.7358	Intermediate Similarity	NPC472586
0.7353	Intermediate Similarity	NPC477041
0.7353	Intermediate Similarity	NPC477044
0.7339	Intermediate Similarity	NPC245756
0.7333	Intermediate Similarity	NPC271862
0.7333	Intermediate Similarity	NPC477548
0.733	Intermediate Similarity	NPC201700
0.7327	Intermediate Similarity	NPC41318
0.7327	Intermediate Similarity	NPC469312
0.7317	Intermediate Similarity	NPC192674
0.7313	Intermediate Similarity	NPC129909
0.731	Intermediate Similarity	NPC19679
0.7277	Intermediate Similarity	NPC55493
0.7277	Intermediate Similarity	NPC267965
0.7273	Intermediate Similarity	NPC470873
0.7268	Intermediate Similarity	NPC50503
0.7264	Intermediate Similarity	NPC204303
0.7259	Intermediate Similarity	NPC192270
0.7254	Intermediate Similarity	NPC6982
0.7245	Intermediate Similarity	NPC213468
0.7236	Intermediate Similarity	NPC473189
0.7236	Intermediate Similarity	NPC280290
0.7233	Intermediate Similarity	NPC241024
0.7233	Intermediate Similarity	NPC477045
0.723	Intermediate Similarity	NPC475778
0.7217	Intermediate Similarity	NPC234999
0.72	Intermediate Similarity	NPC311858
0.7198	Intermediate Similarity	NPC214428
0.7195	Intermediate Similarity	NPC249342
0.7194	Intermediate Similarity	NPC293472
0.7181	Intermediate Similarity	NPC285469
0.7177	Intermediate Similarity	NPC476115
0.7173	Intermediate Similarity	NPC311276
0.7173	Intermediate Similarity	NPC40779
0.7158	Intermediate Similarity	NPC242556
0.7149	Intermediate Similarity	NPC112547
0.7137	Intermediate Similarity	NPC473565
0.7136	Intermediate Similarity	NPC469358
0.7128	Intermediate Similarity	NPC470507
0.7123	Intermediate Similarity	NPC61637
0.712	Intermediate Similarity	NPC16667
0.7117	Intermediate Similarity	NPC183426
0.7115	Intermediate Similarity	NPC252338
0.7113	Intermediate Similarity	NPC280548
0.7097	Intermediate Similarity	NPC124005
0.7097	Intermediate Similarity	NPC37548
0.709	Intermediate Similarity	NPC184476
0.7083	Intermediate Similarity	NPC8104
0.7072	Intermediate Similarity	NPC472762
0.707	Intermediate Similarity	NPC12344
0.7067	Intermediate Similarity	NPC476175
0.7064	Intermediate Similarity	NPC82070
0.7056	Intermediate Similarity	NPC126066
0.7056	Intermediate Similarity	NPC288785
0.7056	Intermediate Similarity	NPC475422
0.7053	Intermediate Similarity	NPC227582
0.705	Intermediate Similarity	NPC139291
0.705	Intermediate Similarity	NPC472108
0.7048	Intermediate Similarity	NPC162730
0.7048	Intermediate Similarity	NPC474116
0.7048	Intermediate Similarity	NPC260900
0.7047	Intermediate Similarity	NPC470508
0.7037	Intermediate Similarity	NPC151781
0.7037	Intermediate Similarity	NPC316181
0.7037	Intermediate Similarity	NPC74562
0.7037	Intermediate Similarity	NPC207726
0.7037	Intermediate Similarity	NPC38736
0.7031	Intermediate Similarity	NPC471583
0.7031	Intermediate Similarity	NPC471782
0.7031	Intermediate Similarity	NPC214106
0.703	Intermediate Similarity	NPC160381
0.7028	Intermediate Similarity	NPC277350
0.7028	Intermediate Similarity	NPC476106
0.7024	Intermediate Similarity	NPC472113
0.7019	Intermediate Similarity	NPC52557
0.7016	Intermediate Similarity	NPC67056
0.7015	Intermediate Similarity	NPC470003
0.701	Intermediate Similarity	NPC472112
0.7005	Intermediate Similarity	NPC189812
0.7005	Intermediate Similarity	NPC329688
0.7005	Intermediate Similarity	NPC187951
0.7	Intermediate Similarity	NPC267423
0.6992	Remote Similarity	NPC131273
0.6992	Remote Similarity	NPC473441
0.6989	Remote Similarity	NPC129042
0.6987	Remote Similarity	NPC278540
0.6986	Remote Similarity	NPC74413
0.6984	Remote Similarity	NPC200743
0.6982	Remote Similarity	NPC475271
0.6967	Remote Similarity	NPC193761
0.6963	Remote Similarity	NPC87755
0.6963	Remote Similarity	NPC299594
0.6961	Remote Similarity	NPC175474
0.696	Remote Similarity	NPC70155
0.6955	Remote Similarity	NPC52254
0.6952	Remote Similarity	NPC477134
0.6946	Remote Similarity	NPC315555
0.6935	Remote Similarity	NPC14325
0.6935	Remote Similarity	NPC28848
0.6934	Remote Similarity	NPC134848
0.6933	Remote Similarity	NPC472589
0.6931	Remote Similarity	NPC472294
0.693	Remote Similarity	NPC475619
0.6927	Remote Similarity	NPC329858
0.6927	Remote Similarity	NPC314333
0.6927	Remote Similarity	NPC95783
0.6923	Remote Similarity	NPC470509
0.692	Remote Similarity	NPC472588
0.6919	Remote Similarity	NPC476044
0.6908	Remote Similarity	NPC267343
0.6907	Remote Similarity	NPC472587
0.6907	Remote Similarity	NPC271734
0.6898	Remote Similarity	NPC303951

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 NPC123019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	563
0.2-0.3	567
0.3-0.4	1807
0.4-0.5	3552
0.5-0.6	1930
0.6-0.7	479
0.7-0.8	10
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
0.7562	Intermediate Similarity	NPD5003	Discontinued
0.7488	Intermediate Similarity	NPD6249	Phase 2
0.7488	Intermediate Similarity	NPD6248	Phase 2
0.7366	Intermediate Similarity	NPD4600	Approved
0.7366	Intermediate Similarity	NPD4601	Approved
0.7317	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD2564	Approved
0.7264	Intermediate Similarity	NPD2565	Phase 2
0.726	Intermediate Similarity	NPD5487	Phase 1
0.7228	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6206	Phase 1
0.72	Intermediate Similarity	NPD5444	Phase 1
0.7184	Intermediate Similarity	NPD6261	Phase 3
0.7143	Intermediate Similarity	NPD5913	Phase 3
0.7143	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5834	Phase 3
0.7089	Intermediate Similarity	NPD5835	Phase 3
0.7083	Intermediate Similarity	NPD7707	Approved
0.7083	Intermediate Similarity	NPD4897	Phase 2
0.7077	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7957	Phase 1
0.7028	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6176	Phase 1
0.7014	Intermediate Similarity	NPD6995	Phase 1
0.7014	Intermediate Similarity	NPD2920	Discontinued
0.6968	Remote Similarity	NPD5506	Approved
0.6968	Remote Similarity	NPD5507	Approved
0.6961	Remote Similarity	NPD4334	Discontinued
0.6927	Remote Similarity	NPD4499	Approved
0.6903	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD2844	Phase 3
0.6884	Remote Similarity	NPD8399	Phase 1
0.6884	Remote Similarity	NPD8423	Phase 2
0.6878	Remote Similarity	NPD4463	Approved
0.6878	Remote Similarity	NPD4462	Approved
0.6872	Remote Similarity	NPD4500	Approved
0.6872	Remote Similarity	NPD4501	Approved
0.6865	Remote Similarity	NPD1592	Phase 3
0.6854	Remote Similarity	NPD3777	Phase 3
0.6853	Remote Similarity	NPD1326	Approved
0.6853	Remote Similarity	NPD1325	Approved
0.6829	Remote Similarity	NPD8431	Approved
0.6816	Remote Similarity	NPD4076	Approved
0.6816	Remote Similarity	NPD4079	Approved
0.6808	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7276	Approved
0.6804	Remote Similarity	NPD7277	Approved
0.6792	Remote Similarity	NPD5427	Suspended
0.6791	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7470	Discontinued
0.6782	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4315	Phase 2
0.6773	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3506	Approved
0.6766	Remote Similarity	NPD3505	Approved
0.6759	Remote Similarity	NPD5429	Discontinued
0.6742	Remote Similarity	NPD3393	Approved
0.6742	Remote Similarity	NPD3394	Approved
0.6742	Remote Similarity	NPD3389	Approved
0.6735	Remote Similarity	NPD6635	Approved
0.6728	Remote Similarity	NPD2509	Approved
0.6728	Remote Similarity	NPD2510	Approved
0.6716	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5596	Phase 2
0.6714	Remote Similarity	NPD6479	Discontinued
0.6713	Remote Similarity	NPD3003	Approved
0.6702	Remote Similarity	NPD3833	Phase 3
0.6702	Remote Similarity	NPD3835	Phase 3
0.67	Remote Similarity	NPD5899	Approved
0.67	Remote Similarity	NPD5898	Approved
0.67	Remote Similarity	NPD43	Approved
0.67	Remote Similarity	NPD5897	Approved
0.67	Remote Similarity	NPD5473	Discontinued
0.67	Remote Similarity	NPD6182	Approved
0.67	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4506	Discontinued
0.6696	Remote Similarity	NPD7796	Approved
0.6696	Remote Similarity	NPD7797	Approved
0.6693	Remote Similarity	NPD8467	Approved
0.6693	Remote Similarity	NPD8427	Approved
0.6693	Remote Similarity	NPD8466	Approved
0.6693	Remote Similarity	NPD8428	Approved
0.6693	Remote Similarity	NPD8429	Approved
0.6693	Remote Similarity	NPD8465	Approved
0.6683	Remote Similarity	NPD7474	Suspended
0.6683	Remote Similarity	NPD6281	Approved
0.6682	Remote Similarity	NPD5512	Phase 3
0.6682	Remote Similarity	NPD7573	Discontinued
0.6681	Remote Similarity	NPD7824	Approved
0.6667	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD56	Approved
0.6667	Remote Similarity	NPD8282	Approved
0.6667	Remote Similarity	NPD8283	Approved
0.6667	Remote Similarity	NPD8160	Phase 2
0.6667	Remote Similarity	NPD5065	Approved
0.6667	Remote Similarity	NPD5901	Discontinued
0.6667	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3390	Phase 2
0.6667	Remote Similarity	NPD6158	Phase 2
0.6652	Remote Similarity	NPD8094	Discontinued
0.6652	Remote Similarity	NPD7688	Phase 1
0.6652	Remote Similarity	NPD6962	Phase 2
0.6652	Remote Similarity	NPD7271	Approved
0.6651	Remote Similarity	NPD6376	Discontinued
0.665	Remote Similarity	NPD8386	Phase 2
0.665	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6026	Approved
0.6637	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7233	Approved
0.6635	Remote Similarity	NPD7234	Approved
0.6635	Remote Similarity	NPD4602	Approved
0.6634	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5104	Approved
0.6625	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5903	Approved
0.6622	Remote Similarity	NPD5902	Approved
0.6621	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7941	Phase 3
0.662	Remote Similarity	NPD7778	Approved
0.662	Remote Similarity	NPD7777	Approved
0.662	Remote Similarity	NPD53	Approved
0.6618	Remote Similarity	NPD6595	Phase 3
0.6617	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7418	Discontinued
0.6606	Remote Similarity	NPD8093	Discontinued
0.6606	Remote Similarity	NPD7454	Approved
0.6606	Remote Similarity	NPD7455	Approved
0.6605	Remote Similarity	NPD4511	Phase 1
0.6601	Remote Similarity	NPD2144	Approved
0.66	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7730	Approved
0.6594	Remote Similarity	NPD7731	Approved
0.6592	Remote Similarity	NPD5612	Discontinued
0.6591	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8426	Approved
0.6588	Remote Similarity	NPD8460	Approved
0.6588	Remote Similarity	NPD8425	Approved
0.6588	Remote Similarity	NPD8459	Approved
0.6585	Remote Similarity	NPD3038	Discontinued
0.6577	Remote Similarity	NPD3794	Approved
0.6577	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3795	Approved
0.6574	Remote Similarity	NPD7187	Phase 2
0.6573	Remote Similarity	NPD7948	Phase 1
0.657	Remote Similarity	NPD5075	Discontinued
0.657	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5140	Approved
0.6566	Remote Similarity	NPD5138	Approved
0.6562	Remote Similarity	NPD5164	Discontinued
0.6561	Remote Similarity	NPD5067	Phase 2
0.6561	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5066	Phase 2
0.656	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1534	Approved
0.6552	Remote Similarity	NPD2382	Approved
0.6552	Remote Similarity	NPD5501	Discontinued
0.6552	Remote Similarity	NPD2380	Approved
0.6552	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2381	Approved
0.6552	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5021	Discontinued
0.655	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6242	Discontinued
0.6544	Remote Similarity	NPD8072	Approved
0.6544	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4880	Discontinued
0.6535	Remote Similarity	NPD7716	Approved
0.6535	Remote Similarity	NPD7717	Approved
0.6531	Remote Similarity	NPD7955	Approved
0.6531	Remote Similarity	NPD7956	Approved
0.653	Remote Similarity	NPD8322	Phase 2
0.653	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5254	Discontinued
0.6524	Remote Similarity	NPD7790	Approved
0.6524	Remote Similarity	NPD7950	Approved
0.6524	Remote Similarity	NPD7952	Approved
0.6524	Remote Similarity	NPD7953	Approved
0.6524	Remote Similarity	NPD7951	Approved
0.6524	Remote Similarity	NPD7791	Approved
0.6524	Remote Similarity	NPD7789	Approved
0.6522	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6987	Phase 1
0.6514	Remote Similarity	NPD8115	Approved
0.6514	Remote Similarity	NPD8114	Approved
0.6512	Remote Similarity	NPD8396	Approved
0.6512	Remote Similarity	NPD1768	Approved
0.6512	Remote Similarity	NPD8395	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