NPASS Compound

Structure

NPC169365 OpenBabel07101718182D 40 44 0 0 1 0 0 0 0 0999 V2000 -4.9207 0.4979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2750 0.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0247 4.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5654 3.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9393 2.3725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0942 1.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1791 4.3530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1893 4.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0887 3.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1182 1.6953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1542 -0.7373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4954 1.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5115 1.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0887 1.2550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1432 3.7198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9858 -1.3262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8482 2.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1432 1.4728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6839 0.1452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6293 2.0963 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5665 1.6368 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3614 2.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7008 0.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5520 2.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7574 -1.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1182 3.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7924 -1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3614 3.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9450 -0.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1791 0.8396 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5665 3.5558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6293 3.0963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1893 0.9819 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5520 2.5963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4123 -2.4110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7416 4.2791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6098 -2.9005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3214 -0.1502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4954 3.5963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 31 1 0 0 0 0 4 31 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 31 1 0 0 0 0 9 32 1 0 0 0 0 10 18 2 0 0 0 0 10 24 1 0 0 0 0 11 19 2 0 0 0 0 11 25 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 30 1 0 0 0 0 15 26 2 0 0 0 0 15 28 1 0 0 0 0 16 27 2 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 17 31 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 32 1 1 0 0 0 21 33 1 1 0 0 0 22 28 2 0 0 0 0 23 29 2 0 0 0 0 24 26 1 0 0 0 0 24 34 2 0 0 0 0 25 27 1 0 0 0 0 25 35 2 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 33 1 6 0 0 0 30 38 1 0 0 0 0 32 5 1 1 0 0 0 32 39 1 0 0 0 0 33 6 1 6 0 0 0 33 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.28
Volume:	574.345
LogP:	4.934
LogD:	3.28
LogS:	-3.599
# Rotatable Bonds:	0
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	5.48
Fsp3:	0.515
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	1.8594699213281274e-05
Pgp-inhibitor:	0.664
Pgp-substrate:	0.194
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.713
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	95.60331726074219%
Volume Distribution (VD):	0.291
Pgp-substrate:	0.6915673017501831%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.301
CYP2C9-inhibitor:	0.501
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.398
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.472
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	3.108
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.184
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.157
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.6
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.692

Download Data

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

Natural Product: NPC169365

Natural Product ID:	NPC169365
*Common Name:**	Eupenifeldin
IUPAC Name:	n.a.
Synonyms:	Eupenifeldin
Standard InCHIKey:	BWTQHPFSWXJOGP-CPQZRDRWSA-N
Standard InCHI:	InChI=1S/C33H40O7/c1-18-10-24(34)26(36)15-28-22(18)12-20-14-30(38)33(6)21(17-31(3,4)8-7-9-32(20,5)39-28)13-23-19(2)11-25(35)27(37)16-29(23)40-33/h7-8,10-11,15-16,20-21,30,38H,9,12-14,17H2,1-6H3,(H,34,36)(H,35,37)/b8-7+/t20-,21-,30-,32-,33-/m1/s1
SMILES:	Cc1cc(=O)c(cc2c1C[C@@H]1C[C@@H](O)[C@]3(C)Oc4cc(O)c(=O)cc(c4C[C@@H]3CC(/C=C/C[C@]1(O2)C)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402418
PubChem CID:	9850499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004150] Hydrocarbon derivatives [CHEMONTID:0001650] Tropones [CHEMONTID:0001674] Tropolones

*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
NPO32537	Unidentified ascomycete	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18095654]
NPO32537	Unidentified ascomycete	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18989977]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4924	Organism	Haemonchus contortus	Haemonchus contortus	EC90	=	50.0	ug ml-1	PMID[486345]

☑ 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 NPC169365 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	368
0.1-0.2	1299
0.2-0.3	3364
0.3-0.4	8082
0.4-0.5	10639
0.5-0.6	4567
0.6-0.7	7663
0.7-0.8	6549
0.8-0.85	158
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC197447
0.8617	High Similarity	NPC60765
0.7941	Intermediate Similarity	NPC120299
0.79	Intermediate Similarity	NPC475098
0.79	Intermediate Similarity	NPC189651
0.7864	Intermediate Similarity	NPC475653
0.7843	Intermediate Similarity	NPC255410
0.7843	Intermediate Similarity	NPC173329
0.7843	Intermediate Similarity	NPC288350
0.7822	Intermediate Similarity	NPC469491
0.7798	Intermediate Similarity	NPC181298
0.7778	Intermediate Similarity	NPC133450
0.7767	Intermediate Similarity	NPC475332
0.7745	Intermediate Similarity	NPC300710
0.7706	Intermediate Similarity	NPC475274
0.77	Intermediate Similarity	NPC3952
0.77	Intermediate Similarity	NPC177668
0.7642	Intermediate Similarity	NPC473596
0.7576	Intermediate Similarity	NPC199382
0.7568	Intermediate Similarity	NPC71680
0.7524	Intermediate Similarity	NPC65700
0.7522	Intermediate Similarity	NPC82759
0.75	Intermediate Similarity	NPC241477
0.7477	Intermediate Similarity	NPC15551
0.7476	Intermediate Similarity	NPC256368
0.7426	Intermediate Similarity	NPC210216
0.7387	Intermediate Similarity	NPC133625
0.7368	Intermediate Similarity	NPC67290
0.7368	Intermediate Similarity	NPC138303
0.7368	Intermediate Similarity	NPC133677
0.7358	Intermediate Similarity	NPC161855
0.7333	Intermediate Similarity	NPC473291
0.73	Intermediate Similarity	NPC61527
0.73	Intermediate Similarity	NPC47220
0.73	Intermediate Similarity	NPC186332
0.73	Intermediate Similarity	NPC311163
0.729	Intermediate Similarity	NPC227865
0.7282	Intermediate Similarity	NPC471324
0.7282	Intermediate Similarity	NPC114172
0.7282	Intermediate Similarity	NPC206679
0.7281	Intermediate Similarity	NPC106395
0.7281	Intermediate Similarity	NPC469463
0.7281	Intermediate Similarity	NPC101400
0.7281	Intermediate Similarity	NPC469454
0.7281	Intermediate Similarity	NPC46269
0.7281	Intermediate Similarity	NPC101965
0.7281	Intermediate Similarity	NPC469496
0.7273	Intermediate Similarity	NPC93026
0.7273	Intermediate Similarity	NPC29389
0.7273	Intermediate Similarity	NPC265502
0.7273	Intermediate Similarity	NPC469960
0.7248	Intermediate Similarity	NPC280566
0.7248	Intermediate Similarity	NPC197736
0.7248	Intermediate Similarity	NPC183570
0.7241	Intermediate Similarity	NPC471145
0.7232	Intermediate Similarity	NPC137911
0.7232	Intermediate Similarity	NPC228477
0.7222	Intermediate Similarity	NPC298233
0.7212	Intermediate Similarity	NPC109406
0.7212	Intermediate Similarity	NPC320552
0.7212	Intermediate Similarity	NPC159092
0.7207	Intermediate Similarity	NPC108682
0.7207	Intermediate Similarity	NPC469957
0.7207	Intermediate Similarity	NPC469959
0.7207	Intermediate Similarity	NPC472263
0.72	Intermediate Similarity	NPC471494
0.72	Intermediate Similarity	NPC11804
0.7193	Intermediate Similarity	NPC313921
0.7193	Intermediate Similarity	NPC98038
0.7193	Intermediate Similarity	NPC123855
0.7193	Intermediate Similarity	NPC138757
0.7193	Intermediate Similarity	NPC76550
0.7184	Intermediate Similarity	NPC327253
0.7182	Intermediate Similarity	NPC272632
0.7172	Intermediate Similarity	NPC288281
0.717	Intermediate Similarity	NPC57664
0.7168	Intermediate Similarity	NPC238850
0.7156	Intermediate Similarity	NPC11956
0.7143	Intermediate Similarity	NPC477241
0.7143	Intermediate Similarity	NPC473807
0.7143	Intermediate Similarity	NPC184208
0.7143	Intermediate Similarity	NPC65829
0.7143	Intermediate Similarity	NPC8538
0.7143	Intermediate Similarity	NPC112868
0.713	Intermediate Similarity	NPC290802
0.7119	Intermediate Similarity	NPC278681
0.7115	Intermediate Similarity	NPC476084
0.7115	Intermediate Similarity	NPC476075
0.7113	Intermediate Similarity	NPC139712
0.7113	Intermediate Similarity	NPC233295
0.7105	Intermediate Similarity	NPC470076
0.7105	Intermediate Similarity	NPC179798
0.7105	Intermediate Similarity	NPC471484
0.7105	Intermediate Similarity	NPC284162
0.7105	Intermediate Similarity	NPC262083
0.7105	Intermediate Similarity	NPC255401
0.7105	Intermediate Similarity	NPC304180
0.71	Intermediate Similarity	NPC78673
0.71	Intermediate Similarity	NPC160517
0.71	Intermediate Similarity	NPC186155
0.7091	Intermediate Similarity	NPC23584
0.7091	Intermediate Similarity	NPC472747
0.7091	Intermediate Similarity	NPC475871
0.7091	Intermediate Similarity	NPC472750
0.7091	Intermediate Similarity	NPC475945
0.7087	Intermediate Similarity	NPC115607
0.7087	Intermediate Similarity	NPC49783
0.7087	Intermediate Similarity	NPC97103
0.7083	Intermediate Similarity	NPC290261
0.7075	Intermediate Similarity	NPC272050
0.7071	Intermediate Similarity	NPC477390
0.7071	Intermediate Similarity	NPC477385
0.7069	Intermediate Similarity	NPC43213
0.7069	Intermediate Similarity	NPC216665
0.7064	Intermediate Similarity	NPC472753
0.7059	Intermediate Similarity	NPC316138
0.7059	Intermediate Similarity	NPC112936
0.7059	Intermediate Similarity	NPC313658
0.7043	Intermediate Similarity	NPC321272
0.7043	Intermediate Similarity	NPC470025
0.7043	Intermediate Similarity	NPC236217
0.7043	Intermediate Similarity	NPC317460
0.7043	Intermediate Similarity	NPC328074
0.7041	Intermediate Similarity	NPC474592
0.7037	Intermediate Similarity	NPC203627
0.7037	Intermediate Similarity	NPC278673
0.7034	Intermediate Similarity	NPC16701
0.703	Intermediate Similarity	NPC67081
0.703	Intermediate Similarity	NPC242233
0.703	Intermediate Similarity	NPC471223
0.7027	Intermediate Similarity	NPC472748
0.7019	Intermediate Similarity	NPC212369
0.7018	Intermediate Similarity	NPC5103
0.7018	Intermediate Similarity	NPC257240
0.7018	Intermediate Similarity	NPC316708
0.701	Intermediate Similarity	NPC477089
0.7009	Intermediate Similarity	NPC478216
0.7009	Intermediate Similarity	NPC16967
0.7	Intermediate Similarity	NPC49208
0.7	Intermediate Similarity	NPC474747
0.7	Intermediate Similarity	NPC23748
0.7	Intermediate Similarity	NPC161045
0.7	Intermediate Similarity	NPC44261
0.7	Intermediate Similarity	NPC472754
0.6991	Remote Similarity	NPC50124
0.6983	Remote Similarity	NPC56448
0.6983	Remote Similarity	NPC321496
0.6983	Remote Similarity	NPC470027
0.6981	Remote Similarity	NPC120351
0.6981	Remote Similarity	NPC471994
0.6981	Remote Similarity	NPC166143
0.6979	Remote Similarity	NPC256720
0.6979	Remote Similarity	NPC236228
0.6975	Remote Similarity	NPC213761
0.6975	Remote Similarity	NPC35171
0.6975	Remote Similarity	NPC219656
0.6972	Remote Similarity	NPC79631
0.6972	Remote Similarity	NPC475053
0.6972	Remote Similarity	NPC38855
0.697	Remote Similarity	NPC474894
0.697	Remote Similarity	NPC315731
0.6967	Remote Similarity	NPC145238
0.6964	Remote Similarity	NPC477125
0.6964	Remote Similarity	NPC472749
0.6964	Remote Similarity	NPC472751
0.6964	Remote Similarity	NPC471206
0.6964	Remote Similarity	NPC172867
0.6964	Remote Similarity	NPC469852
0.6957	Remote Similarity	NPC324683
0.6957	Remote Similarity	NPC17791
0.6957	Remote Similarity	NPC317107
0.6957	Remote Similarity	NPC470026
0.6952	Remote Similarity	NPC303697
0.6952	Remote Similarity	NPC45579
0.6949	Remote Similarity	NPC23046
0.6949	Remote Similarity	NPC157380
0.6949	Remote Similarity	NPC185287
0.6944	Remote Similarity	NPC205143
0.6944	Remote Similarity	NPC202705
0.6944	Remote Similarity	NPC239895
0.6944	Remote Similarity	NPC20066
0.6942	Remote Similarity	NPC257017
0.6942	Remote Similarity	NPC162009
0.6939	Remote Similarity	NPC476701
0.6939	Remote Similarity	NPC470148
0.6939	Remote Similarity	NPC470149
0.6937	Remote Similarity	NPC473624
0.6937	Remote Similarity	NPC472755
0.6937	Remote Similarity	NPC4620
0.6937	Remote Similarity	NPC194323
0.6937	Remote Similarity	NPC476848
0.6931	Remote Similarity	NPC83702
0.693	Remote Similarity	NPC471400
0.693	Remote Similarity	NPC47951
0.693	Remote Similarity	NPC477102
0.693	Remote Similarity	NPC38154
0.6923	Remote Similarity	NPC265290
0.6923	Remote Similarity	NPC305044
0.6917	Remote Similarity	NPC19336
0.6917	Remote Similarity	NPC329080

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 NPC169365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	854
0.2-0.3	1711
0.3-0.4	2640
0.4-0.5	2016
0.5-0.6	1099
0.6-0.7	421
0.7-0.8	86
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7525	Intermediate Similarity	NPD7838	Discovery
0.7196	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6371	Approved
0.6909	Remote Similarity	NPD5344	Discontinued
0.686	Remote Similarity	NPD7503	Approved
0.6822	Remote Similarity	NPD5282	Discontinued
0.6818	Remote Similarity	NPD6648	Approved
0.6754	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7524	Approved
0.6698	Remote Similarity	NPD6698	Approved
0.6698	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6602	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6686	Approved
0.6525	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6695	Phase 3
0.6481	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD4225	Approved
0.6415	Remote Similarity	NPD7750	Discontinued
0.6373	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6933	Approved
0.6283	Remote Similarity	NPD7638	Approved
0.626	Remote Similarity	NPD7115	Discovery
0.626	Remote Similarity	NPD7260	Phase 2
0.6228	Remote Similarity	NPD7639	Approved
0.6228	Remote Similarity	NPD7640	Approved
0.6214	Remote Similarity	NPD6931	Approved
0.6214	Remote Similarity	NPD7514	Phase 3
0.6214	Remote Similarity	NPD6930	Phase 2
0.6214	Remote Similarity	NPD7332	Phase 2
0.62	Remote Similarity	NPD8264	Approved
0.619	Remote Similarity	NPD8033	Approved
0.6182	Remote Similarity	NPD7637	Suspended
0.6161	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4632	Approved
0.6132	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5778	Approved
0.6126	Remote Similarity	NPD5779	Approved
0.6117	Remote Similarity	NPD6929	Approved
0.6111	Remote Similarity	NPD8294	Approved
0.6111	Remote Similarity	NPD8377	Approved
0.61	Remote Similarity	NPD6926	Approved
0.61	Remote Similarity	NPD6924	Approved
0.6091	Remote Similarity	NPD5785	Approved
0.608	Remote Similarity	NPD7328	Approved
0.608	Remote Similarity	NPD7327	Approved
0.6078	Remote Similarity	NPD6932	Approved
0.6066	Remote Similarity	NPD8297	Approved
0.6063	Remote Similarity	NPD8378	Approved
0.6063	Remote Similarity	NPD8296	Approved
0.6063	Remote Similarity	NPD8380	Approved
0.6063	Remote Similarity	NPD8335	Approved
0.6063	Remote Similarity	NPD8379	Approved
0.6063	Remote Similarity	NPD8513	Phase 3
0.6058	Remote Similarity	NPD4695	Discontinued
0.605	Remote Similarity	NPD6412	Phase 2
0.6036	Remote Similarity	NPD7087	Discontinued
0.6032	Remote Similarity	NPD7516	Approved
0.6019	Remote Similarity	NPD7145	Approved
0.6019	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6902	Approved
0.5984	Remote Similarity	NPD6054	Approved
0.5984	Remote Similarity	NPD6319	Approved
0.5966	Remote Similarity	NPD6640	Phase 3
0.5963	Remote Similarity	NPD4251	Approved
0.5963	Remote Similarity	NPD4250	Approved
0.595	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5209	Approved
0.5938	Remote Similarity	NPD8516	Approved
0.5938	Remote Similarity	NPD8515	Approved
0.5938	Remote Similarity	NPD8517	Approved
0.5926	Remote Similarity	NPD1696	Phase 3
0.5926	Remote Similarity	NPD6893	Approved
0.5922	Remote Similarity	NPD6925	Approved
0.5922	Remote Similarity	NPD5776	Phase 2
0.5912	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7509	Discontinued
0.5902	Remote Similarity	NPD4634	Approved
0.5893	Remote Similarity	NPD6411	Approved
0.5891	Remote Similarity	NPD6370	Approved
0.5873	Remote Similarity	NPD6009	Approved
0.5872	Remote Similarity	NPD4249	Approved
0.5868	Remote Similarity	NPD6899	Approved
0.5868	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8130	Phase 1
0.5852	Remote Similarity	NPD6845	Suspended
0.5849	Remote Similarity	NPD6898	Phase 1
0.5847	Remote Similarity	NPD5211	Phase 2
0.5846	Remote Similarity	NPD7830	Approved
0.5846	Remote Similarity	NPD7829	Approved
0.5846	Remote Similarity	NPD7604	Phase 2
0.5826	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5983	Phase 2
0.5814	Remote Similarity	NPD6015	Approved
0.5814	Remote Similarity	NPD6016	Approved
0.5812	Remote Similarity	NPD4696	Approved
0.5812	Remote Similarity	NPD5285	Approved
0.5812	Remote Similarity	NPD5286	Approved
0.581	Remote Similarity	NPD6683	Phase 2
0.5802	Remote Similarity	NPD7492	Approved
0.58	Remote Similarity	NPD7143	Approved
0.58	Remote Similarity	NPD7144	Approved
0.5794	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7736	Approved
0.5785	Remote Similarity	NPD5697	Approved
0.578	Remote Similarity	NPD1694	Approved
0.5776	Remote Similarity	NPD6084	Phase 2
0.5776	Remote Similarity	NPD6083	Phase 2
0.5772	Remote Similarity	NPD7102	Approved
0.5772	Remote Similarity	NPD6883	Approved
0.5772	Remote Similarity	NPD7290	Approved
0.5769	Remote Similarity	NPD5988	Approved
0.5769	Remote Similarity	NPD4756	Discovery
0.5763	Remote Similarity	NPD5223	Approved
0.5758	Remote Similarity	NPD7507	Approved
0.5758	Remote Similarity	NPD8273	Phase 1
0.5758	Remote Similarity	NPD6336	Discontinued
0.5758	Remote Similarity	NPD6616	Approved
0.575	Remote Similarity	NPD5141	Approved
0.5748	Remote Similarity	NPD7500	Approved
0.5743	Remote Similarity	NPD7151	Approved
0.5743	Remote Similarity	NPD7150	Approved
0.5743	Remote Similarity	NPD7152	Approved
0.5741	Remote Similarity	NPD7154	Phase 3
0.5739	Remote Similarity	NPD4629	Approved
0.5739	Remote Similarity	NPD5210	Approved
0.5738	Remote Similarity	NPD6011	Approved
0.5736	Remote Similarity	NPD6059	Approved
0.5728	Remote Similarity	NPD8039	Approved
0.5726	Remote Similarity	NPD6649	Approved
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6847	Approved
0.5726	Remote Similarity	NPD6650	Approved
0.5725	Remote Similarity	NPD8328	Phase 3
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6101	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD5226	Approved
0.5702	Remote Similarity	NPD6402	Approved
0.5702	Remote Similarity	NPD7128	Approved
0.5702	Remote Similarity	NPD6675	Approved
0.5702	Remote Similarity	NPD5739	Approved
0.57	Remote Similarity	NPD6923	Approved
0.57	Remote Similarity	NPD6922	Approved
0.5691	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD6013	Approved
0.5691	Remote Similarity	NPD6014	Approved
0.569	Remote Similarity	NPD7839	Suspended
0.569	Remote Similarity	NPD5221	Approved
0.569	Remote Similarity	NPD5222	Approved
0.569	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4732	Discontinued
0.568	Remote Similarity	NPD6882	Approved
0.5667	Remote Similarity	NPD5174	Approved
0.5667	Remote Similarity	NPD5175	Approved
0.566	Remote Similarity	NPD4195	Approved
0.5652	Remote Similarity	NPD7748	Approved
0.5645	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7902	Approved
0.5641	Remote Similarity	NPD5173	Approved
0.5641	Remote Similarity	NPD4755	Approved
0.5639	Remote Similarity	NPD8451	Approved
0.5636	Remote Similarity	NPD5363	Approved
0.5636	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7319	Approved
0.5625	Remote Similarity	NPD4198	Discontinued
0.5625	Remote Similarity	NPD7505	Discontinued
0.5615	Remote Similarity	NPD7741	Discontinued
0.5614	Remote Similarity	NPD6079	Approved
0.5612	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7320	Approved
0.5607	Remote Similarity	NPD4820	Approved
0.5607	Remote Similarity	NPD4821	Approved
0.5607	Remote Similarity	NPD4819	Approved
0.5607	Remote Similarity	NPD7525	Registered
0.5607	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD4822	Approved
0.5603	Remote Similarity	NPD5695	Phase 3

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