NPASS Compound

Structure

NPC166116 OpenBabel07101719512D 37 42 0 0 1 0 0 0 0 0999 V2000 -0.8684 -3.0213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0776 -4.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6591 -4.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6591 -2.5648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6454 -1.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6454 -3.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0776 -5.3039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6591 -5.3039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5584 -1.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5584 -3.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4498 -1.1952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4498 -1.7595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6591 0.1744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6591 -3.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8684 -3.9343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1888 -2.2160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6591 -1.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8684 -5.7604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0149 -2.2160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4498 -0.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4498 -2.6725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6591 -1.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8684 -0.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8684 -2.6725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8684 -1.1952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8684 -1.7595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5367 -2.2160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5367 -0.7387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.4773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8684 -6.6735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9280 -2.2160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2405 0.1744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2405 -3.1290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6591 0.5231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4497 -0.7387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9547 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 4 2 0 0 0 0 1 15 1 0 0 0 0 2 7 1 0 0 0 0 2 15 2 0 0 0 0 3 8 2 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 12 22 1 0 0 0 0 13 20 2 0 0 0 0 13 23 1 0 0 0 0 14 21 1 0 0 0 0 14 24 2 0 0 0 0 16 27 1 0 0 0 0 17 25 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 26 2 0 0 0 0 22 34 1 0 0 0 0 23 25 2 0 0 0 0 23 37 1 0 0 0 0 24 26 1 0 0 0 0 24 36 1 0 0 0 0 26 29 1 0 0 0 0 27 29 1 6 0 0 0 27 36 1 0 0 0 0 28 29 1 0 0 0 0 28 35 2 0 0 0 0 28 37 1 0 0 0 0 29 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.12
Volume:	492.213
LogP:	4.164
LogD:	3.787
LogS:	-4.081
# Rotatable Bonds:	3
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	4.358
Fsp3:	0.069
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.718
MDCK Permeability:	9.011325346364174e-06
Pgp-inhibitor:	0.333
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.1494369506836%
Volume Distribution (VD):	0.53
Pgp-substrate:	1.546387791633606%

ADMET: Metabolism

CYP1A2-inhibitor:	0.274
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.956
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.832
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.393
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	13.447
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.618
AMES Toxicity:	0.879
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.964
Carcinogencity:	0.517
Eye Corrosion:	0.003
Eye Irritation:	0.89
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC166116

Natural Product ID:	NPC166116
*Common Name:**	Yuccaol B
IUPAC Name:	(2'R,3R)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]spiro[1-benzofuran-3,3'-2H-1-benzofuran]-2-one
Synonyms:
Standard InCHIKey:	YOJXOIWMUVWNAB-MPTTXDELSA-N
Standard InCHI:	InChI=1S/C29H20O8/c30-18-7-2-15(3-8-18)1-4-17-11-20(32)13-23-25(17)29(28(35)37-23)26-22(34)12-21(33)14-24(26)36-27(29)16-5-9-19(31)10-6-16/h1-14,27,30-34H/b4-1+/t27-,29-/m1/s1
SMILES:	C(=Cc1cc(cc2c1[C@]1(c3c(cc(cc3O[C@@H]1c1ccc(cc1)O)O)O)C(=O)O2)O)/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469643
PubChem CID:	10345709
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO1943	Yucca schidigera	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757713]
NPO1943	Yucca schidigera	Species	Asparagaceae	Eukaryota	bark	n.a.	n.a.	PMID[15165156]
NPO1943	Yucca schidigera	Species	Asparagaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.093	mM	PMID[489848]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	76.3	%	PMID[489848]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	72.1	%	PMID[489848]

☑ 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 NPC166116 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	375
0.1-0.2	1597
0.2-0.3	3272
0.3-0.4	8632
0.4-0.5	10287
0.5-0.6	3777
0.6-0.7	6302
0.7-0.8	7983
0.8-0.85	453
0.85-0.9	13
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55463
0.9427	High Similarity	NPC215802
0.9427	High Similarity	NPC167231
0.9308	High Similarity	NPC91043
0.9231	High Similarity	NPC186228
0.8528	High Similarity	NPC214279
0.8523	High Similarity	NPC11727
0.8523	High Similarity	NPC15109
0.8519	High Similarity	NPC90822
0.8509	High Similarity	NPC218818
0.85	High Similarity	NPC146211
0.8476	Intermediate Similarity	NPC474591
0.8466	Intermediate Similarity	NPC192258
0.8466	Intermediate Similarity	NPC476200
0.8466	Intermediate Similarity	NPC55121
0.8466	Intermediate Similarity	NPC174311
0.8462	Intermediate Similarity	NPC12305
0.8462	Intermediate Similarity	NPC17101
0.8462	Intermediate Similarity	NPC77903
0.8428	Intermediate Similarity	NPC473236
0.8421	Intermediate Similarity	NPC213607
0.8421	Intermediate Similarity	NPC174787
0.8421	Intermediate Similarity	NPC182509
0.8418	Intermediate Similarity	NPC309979
0.8418	Intermediate Similarity	NPC307780
0.8408	Intermediate Similarity	NPC106328
0.8408	Intermediate Similarity	NPC35150
0.8405	Intermediate Similarity	NPC139540
0.8405	Intermediate Similarity	NPC301256
0.8405	Intermediate Similarity	NPC312273
0.8405	Intermediate Similarity	NPC177100
0.8395	Intermediate Similarity	NPC239118
0.8395	Intermediate Similarity	NPC4950
0.8387	Intermediate Similarity	NPC71739
0.8387	Intermediate Similarity	NPC149633
0.8383	Intermediate Similarity	NPC477572
0.8383	Intermediate Similarity	NPC477573
0.8383	Intermediate Similarity	NPC477571
0.8354	Intermediate Similarity	NPC473012
0.8354	Intermediate Similarity	NPC473011
0.8344	Intermediate Similarity	NPC141717
0.8344	Intermediate Similarity	NPC119910
0.8333	Intermediate Similarity	NPC158542
0.8333	Intermediate Similarity	NPC134621
0.8333	Intermediate Similarity	NPC71686
0.8333	Intermediate Similarity	NPC176804
0.8323	Intermediate Similarity	NPC476279
0.8323	Intermediate Similarity	NPC41494
0.8323	Intermediate Similarity	NPC216403
0.8323	Intermediate Similarity	NPC304894
0.8323	Intermediate Similarity	NPC186100
0.8323	Intermediate Similarity	NPC258474
0.8323	Intermediate Similarity	NPC201227
0.8323	Intermediate Similarity	NPC15659
0.8313	Intermediate Similarity	NPC30027
0.8313	Intermediate Similarity	NPC82330
0.8312	Intermediate Similarity	NPC307287
0.8303	Intermediate Similarity	NPC473009
0.8294	Intermediate Similarity	NPC324220
0.8294	Intermediate Similarity	NPC312630
0.8291	Intermediate Similarity	NPC146388
0.8291	Intermediate Similarity	NPC125570
0.8282	Intermediate Similarity	NPC329743
0.828	Intermediate Similarity	NPC242774
0.828	Intermediate Similarity	NPC231712
0.828	Intermediate Similarity	NPC237546
0.828	Intermediate Similarity	NPC111134
0.828	Intermediate Similarity	NPC224921
0.828	Intermediate Similarity	NPC6702
0.828	Intermediate Similarity	NPC133209
0.828	Intermediate Similarity	NPC237208
0.828	Intermediate Similarity	NPC112819
0.8278	Intermediate Similarity	NPC125579
0.8272	Intermediate Similarity	NPC32867
0.8272	Intermediate Similarity	NPC137100
0.8272	Intermediate Similarity	NPC69531
0.8272	Intermediate Similarity	NPC198489
0.8272	Intermediate Similarity	NPC61112
0.8272	Intermediate Similarity	NPC309648
0.8272	Intermediate Similarity	NPC318432
0.8269	Intermediate Similarity	NPC95123
0.8269	Intermediate Similarity	NPC470932
0.8269	Intermediate Similarity	NPC66404
0.8258	Intermediate Similarity	NPC173203
0.8258	Intermediate Similarity	NPC163508
0.8253	Intermediate Similarity	NPC473010
0.825	Intermediate Similarity	NPC317715
0.825	Intermediate Similarity	NPC240768
0.825	Intermediate Similarity	NPC204561
0.825	Intermediate Similarity	NPC309512
0.825	Intermediate Similarity	NPC78835
0.825	Intermediate Similarity	NPC148945
0.825	Intermediate Similarity	NPC316960
0.825	Intermediate Similarity	NPC200773
0.8242	Intermediate Similarity	NPC144557
0.8242	Intermediate Similarity	NPC261896
0.8235	Intermediate Similarity	NPC300657
0.8232	Intermediate Similarity	NPC292863
0.8232	Intermediate Similarity	NPC310399
0.8232	Intermediate Similarity	NPC73422
0.8232	Intermediate Similarity	NPC24164
0.8232	Intermediate Similarity	NPC184326
0.8228	Intermediate Similarity	NPC142863
0.8224	Intermediate Similarity	NPC223616
0.8221	Intermediate Similarity	NPC289322
0.8221	Intermediate Similarity	NPC318527
0.8221	Intermediate Similarity	NPC19947
0.8221	Intermediate Similarity	NPC323627
0.8221	Intermediate Similarity	NPC324358
0.8221	Intermediate Similarity	NPC287789
0.8221	Intermediate Similarity	NPC114179
0.8221	Intermediate Similarity	NPC207584
0.8221	Intermediate Similarity	NPC322459
0.8221	Intermediate Similarity	NPC160512
0.8221	Intermediate Similarity	NPC271741
0.8221	Intermediate Similarity	NPC38779
0.8221	Intermediate Similarity	NPC68324
0.8221	Intermediate Similarity	NPC156818
0.8217	Intermediate Similarity	NPC131766
0.8217	Intermediate Similarity	NPC14468
0.8217	Intermediate Similarity	NPC29577
0.821	Intermediate Similarity	NPC66441
0.821	Intermediate Similarity	NPC125709
0.821	Intermediate Similarity	NPC300668
0.821	Intermediate Similarity	NPC292385
0.821	Intermediate Similarity	NPC254351
0.821	Intermediate Similarity	NPC182555
0.821	Intermediate Similarity	NPC134171
0.8204	Intermediate Similarity	NPC477835
0.8199	Intermediate Similarity	NPC273483
0.8199	Intermediate Similarity	NPC174086
0.8199	Intermediate Similarity	NPC476154
0.8199	Intermediate Similarity	NPC474656
0.8199	Intermediate Similarity	NPC474843
0.8199	Intermediate Similarity	NPC207624
0.8199	Intermediate Similarity	NPC65591
0.8199	Intermediate Similarity	NPC178574
0.8193	Intermediate Similarity	NPC38591
0.8193	Intermediate Similarity	NPC272750
0.8193	Intermediate Similarity	NPC134047
0.8193	Intermediate Similarity	NPC173729
0.8193	Intermediate Similarity	NPC223006
0.8187	Intermediate Similarity	NPC295036
0.8187	Intermediate Similarity	NPC60413
0.8187	Intermediate Similarity	NPC470107
0.8187	Intermediate Similarity	NPC476185
0.8187	Intermediate Similarity	NPC475460
0.8187	Intermediate Similarity	NPC321896
0.8182	Intermediate Similarity	NPC288149
0.8182	Intermediate Similarity	NPC90336
0.8182	Intermediate Similarity	NPC92589
0.8182	Intermediate Similarity	NPC137232
0.8182	Intermediate Similarity	NPC18380
0.8171	Intermediate Similarity	NPC195167
0.8171	Intermediate Similarity	NPC55443
0.8171	Intermediate Similarity	NPC98083
0.8171	Intermediate Similarity	NPC18699
0.8171	Intermediate Similarity	NPC209473
0.8171	Intermediate Similarity	NPC7543
0.8171	Intermediate Similarity	NPC24339
0.8171	Intermediate Similarity	NPC94220
0.8171	Intermediate Similarity	NPC166456
0.8171	Intermediate Similarity	NPC295090
0.8171	Intermediate Similarity	NPC36354
0.8166	Intermediate Similarity	NPC180768
0.8165	Intermediate Similarity	NPC267509
0.816	Intermediate Similarity	NPC88803
0.816	Intermediate Similarity	NPC250436
0.816	Intermediate Similarity	NPC165483
0.816	Intermediate Similarity	NPC104983
0.816	Intermediate Similarity	NPC300845
0.816	Intermediate Similarity	NPC237946
0.816	Intermediate Similarity	NPC291948
0.816	Intermediate Similarity	NPC32373
0.8155	Intermediate Similarity	NPC473818
0.8153	Intermediate Similarity	NPC295696
0.8148	Intermediate Similarity	NPC62903
0.8148	Intermediate Similarity	NPC7178
0.8144	Intermediate Similarity	NPC222531
0.8144	Intermediate Similarity	NPC469664
0.8141	Intermediate Similarity	NPC250755
0.8141	Intermediate Similarity	NPC105648
0.814	Intermediate Similarity	NPC478000
0.814	Intermediate Similarity	NPC475783
0.8137	Intermediate Similarity	NPC58668
0.8137	Intermediate Similarity	NPC193976
0.8137	Intermediate Similarity	NPC476391
0.8137	Intermediate Similarity	NPC106372
0.8137	Intermediate Similarity	NPC290671
0.8137	Intermediate Similarity	NPC39819
0.8137	Intermediate Similarity	NPC215921
0.8137	Intermediate Similarity	NPC133856
0.8137	Intermediate Similarity	NPC115324
0.8137	Intermediate Similarity	NPC56184
0.8137	Intermediate Similarity	NPC70016
0.8137	Intermediate Similarity	NPC23668
0.8137	Intermediate Similarity	NPC476434
0.8133	Intermediate Similarity	NPC249070
0.8133	Intermediate Similarity	NPC477239
0.8133	Intermediate Similarity	NPC3448

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 NPC166116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	899
0.2-0.3	1663
0.3-0.4	2626
0.4-0.5	1851
0.5-0.6	1111
0.6-0.7	480
0.7-0.8	174
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD3749	Approved
0.8217	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8171	Intermediate Similarity	NPD6234	Discontinued
0.816	Intermediate Similarity	NPD4965	Approved
0.816	Intermediate Similarity	NPD7768	Phase 2
0.816	Intermediate Similarity	NPD4966	Approved
0.816	Intermediate Similarity	NPD4967	Phase 2
0.816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3750	Approved
0.8037	Intermediate Similarity	NPD7819	Suspended
0.7975	Intermediate Similarity	NPD37	Approved
0.7964	Intermediate Similarity	NPD7199	Phase 2
0.7941	Intermediate Similarity	NPD7228	Approved
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7229	Phase 3
0.7917	Intermediate Similarity	NPD6232	Discontinued
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7895	Intermediate Similarity	NPD5844	Phase 1
0.7879	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.787	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD4908	Phase 1
0.7803	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5402	Approved
0.7756	Intermediate Similarity	NPD3748	Approved
0.7733	Intermediate Similarity	NPD3818	Discontinued
0.7722	Intermediate Similarity	NPD1549	Phase 2
0.7722	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6166	Phase 2
0.7719	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6273	Approved
0.7712	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8455	Phase 2
0.7711	Intermediate Similarity	NPD1465	Phase 2
0.7711	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3226	Approved
0.7679	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7075	Discontinued
0.767	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD8312	Approved
0.7657	Intermediate Similarity	NPD6559	Discontinued
0.7654	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1934	Approved
0.7636	Intermediate Similarity	NPD4380	Phase 2
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3787	Discontinued
0.7597	Intermediate Similarity	NPD3764	Approved
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7595	Intermediate Similarity	NPD6100	Approved
0.7595	Intermediate Similarity	NPD6099	Approved
0.7576	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5403	Approved
0.756	Intermediate Similarity	NPD3817	Phase 2
0.7557	Intermediate Similarity	NPD7240	Approved
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.7532	Intermediate Similarity	NPD1510	Phase 2
0.753	Intermediate Similarity	NPD6599	Discontinued
0.7515	Intermediate Similarity	NPD3882	Suspended
0.7514	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1511	Approved
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5494	Approved
0.7484	Intermediate Similarity	NPD5404	Approved
0.7484	Intermediate Similarity	NPD2796	Approved
0.7484	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5408	Approved
0.7484	Intermediate Similarity	NPD5406	Approved
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD5405	Approved
0.7484	Intermediate Similarity	NPD6798	Discontinued
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7459	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2800	Approved
0.7443	Intermediate Similarity	NPD7074	Phase 3
0.7442	Intermediate Similarity	NPD8127	Discontinued
0.744	Intermediate Similarity	NPD6801	Discontinued
0.7439	Intermediate Similarity	NPD5401	Approved
0.7407	Intermediate Similarity	NPD7003	Approved
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7403	Intermediate Similarity	NPD2861	Phase 2
0.7394	Intermediate Similarity	NPD1512	Approved
0.7389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1613	Approved
0.7389	Intermediate Similarity	NPD4140	Approved
0.7386	Intermediate Similarity	NPD7054	Approved
0.7386	Intermediate Similarity	NPD2797	Approved
0.7378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6799	Approved
0.7378	Intermediate Similarity	NPD7390	Discontinued
0.7363	Intermediate Similarity	NPD4287	Approved
0.7349	Intermediate Similarity	NPD920	Approved
0.7345	Intermediate Similarity	NPD7472	Approved
0.7342	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3751	Discontinued
0.7329	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6004	Phase 3
0.7329	Intermediate Similarity	NPD6002	Phase 3
0.7329	Intermediate Similarity	NPD6005	Phase 3
0.7325	Intermediate Similarity	NPD8032	Phase 2
0.7325	Intermediate Similarity	NPD6233	Phase 2
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7303	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD1608	Approved
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4060	Phase 1
0.7278	Intermediate Similarity	NPD1240	Approved
0.7273	Intermediate Similarity	NPD1203	Approved
0.7263	Intermediate Similarity	NPD7251	Discontinued
0.7261	Intermediate Similarity	NPD3268	Approved
0.7251	Intermediate Similarity	NPD4288	Approved
0.7246	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7808	Phase 3
0.7215	Intermediate Similarity	NPD6663	Approved
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3225	Approved
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.7197	Intermediate Similarity	NPD7095	Approved
0.7195	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1607	Approved
0.7184	Intermediate Similarity	NPD6746	Phase 2
0.7179	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7680	Approved
0.7168	Intermediate Similarity	NPD6971	Discontinued
0.716	Intermediate Similarity	NPD4476	Approved
0.716	Intermediate Similarity	NPD4477	Approved
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7427	Discontinued
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7135	Intermediate Similarity	NPD7177	Discontinued
0.7134	Intermediate Similarity	NPD1243	Approved
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2344	Approved
0.7111	Intermediate Similarity	NPD5953	Discontinued
0.7105	Intermediate Similarity	NPD1778	Approved
0.7105	Intermediate Similarity	NPD17	Approved
0.7102	Intermediate Similarity	NPD7315	Approved
0.7101	Intermediate Similarity	NPD1653	Approved
0.7097	Intermediate Similarity	NPD1283	Approved
0.7093	Intermediate Similarity	NPD5761	Phase 2
0.7093	Intermediate Similarity	NPD5760	Phase 2
0.7091	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4110	Phase 3
0.7089	Intermediate Similarity	NPD3027	Phase 3
0.7078	Intermediate Similarity	NPD1481	Phase 2
0.707	Intermediate Similarity	NPD5736	Approved
0.7063	Intermediate Similarity	NPD2979	Phase 3
0.7062	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2438	Suspended
0.7048	Intermediate Similarity	NPD6190	Approved
0.7044	Intermediate Similarity	NPD1296	Phase 2
0.7039	Intermediate Similarity	NPD5585	Approved
0.7032	Intermediate Similarity	NPD4749	Approved
0.7029	Intermediate Similarity	NPD919	Approved
0.7024	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD447	Suspended
0.7013	Intermediate Similarity	NPD1535	Discovery
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.7	Intermediate Similarity	NPD7286	Phase 2
0.6994	Remote Similarity	NPD4308	Phase 3
0.6994	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8151	Discontinued
0.6978	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1894	Discontinued
0.6968	Remote Similarity	NPD9717	Approved
0.6964	Remote Similarity	NPD7212	Phase 2
0.6964	Remote Similarity	NPD7213	Phase 3
0.6959	Remote Similarity	NPD7458	Discontinued
0.6946	Remote Similarity	NPD2309	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