NPASS Compound

Structure

NPC476452 OpenBabel07101718192D 34 38 0 0 1 0 0 0 0 0999 V2000 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 0.0320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 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 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 2.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 3 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 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 3.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 0.2399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 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 14 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 28 2 0 0 0 0 14 32 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 17 29 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 6 0 0 0 19 26 1 6 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 32 1 6 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 22 34 1 0 0 0 0 23 30 1 0 0 0 0 23 33 1 0 0 0 0 24 31 1 0 0 0 0 24 33 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 1 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.26
Volume:	483.752
LogP:	4.113
LogD:	3.455
LogS:	-4.766
# Rotatable Bonds:	4
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	4.873
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.793
MDCK Permeability:	1.4180745893099811e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.145
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	86.70755004882812%
Volume Distribution (VD):	0.947
Pgp-substrate:	23.505884170532227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.864
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	2.362
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.357
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.518
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.21
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC476452

Natural Product ID:	NPC476452
*Common Name:**	QWMFMXXBQRMPTO-KAPPIMGASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QWMFMXXBQRMPTO-KAPPIMGASA-N
Standard InCHI:	InChI=1S/C27H38O7/c1-14(28)32-20-9-10-26(4)18(25(20,2)3)8-11-27(5)19(26)13-15-17(29)12-16-21(22(15)34-27)24(31-7)33-23(16)30-6/h12,18-20,23-24,29H,8-11,13H2,1-7H3/t18-,19+,20-,23?,24?,26-,27-/m0/s1
SMILES:	COC1OC(c2c1c1O[C@@]3(C)CC[C@@H]4[C@]([C@H]3Cc1c(c2)O)(C)CC[C@@H](C4(C)C)OC(=O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL63084
PubChem CID:	9891061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001828] Isoflavanols

*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
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341709]
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9873488]
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	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
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	7000.0	nM	PMID[537008]
NPT2	Others	Unspecified		IC50	n.a.	100000.0	nM	PMID[537008]

☑ 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 NPC476452 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	343
0.1-0.2	1545
0.2-0.3	3247
0.3-0.4	7045
0.4-0.5	10078
0.5-0.6	6304
0.6-0.7	8946
0.7-0.8	4934
0.8-0.85	236
0.85-0.9	17
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9448	High Similarity	NPC471608
0.8846	High Similarity	NPC239118
0.875	High Similarity	NPC470208
0.875	High Similarity	NPC295573
0.8726	High Similarity	NPC4950
0.8716	High Similarity	NPC5155
0.8684	High Similarity	NPC95990
0.8662	High Similarity	NPC158542
0.8627	High Similarity	NPC181452
0.8627	High Similarity	NPC220006
0.8621	High Similarity	NPC24913
0.8621	High Similarity	NPC177712
0.8581	High Similarity	NPC302610
0.8571	High Similarity	NPC24425
0.8571	High Similarity	NPC183380
0.8562	High Similarity	NPC159697
0.8562	High Similarity	NPC117788
0.8562	High Similarity	NPC130959
0.8562	High Similarity	NPC290902
0.8562	High Similarity	NPC474795
0.8562	High Similarity	NPC291326
0.8562	High Similarity	NPC474940
0.8562	High Similarity	NPC474856
0.8562	High Similarity	NPC474834
0.8562	High Similarity	NPC303013
0.8506	High Similarity	NPC475940
0.8506	High Similarity	NPC474893
0.8503	High Similarity	NPC137580
0.8491	Intermediate Similarity	NPC218818
0.8487	Intermediate Similarity	NPC90645
0.8483	Intermediate Similarity	NPC181497
0.8483	Intermediate Similarity	NPC271945
0.8472	Intermediate Similarity	NPC25729
0.8472	Intermediate Similarity	NPC474494
0.8467	Intermediate Similarity	NPC472791
0.8467	Intermediate Similarity	NPC472792
0.8462	Intermediate Similarity	NPC233467
0.8462	Intermediate Similarity	NPC59692
0.8457	Intermediate Similarity	NPC222531
0.8452	Intermediate Similarity	NPC162976
0.8452	Intermediate Similarity	NPC472710
0.8452	Intermediate Similarity	NPC218041
0.8452	Intermediate Similarity	NPC469707
0.8452	Intermediate Similarity	NPC214326
0.8452	Intermediate Similarity	NPC472709
0.8452	Intermediate Similarity	NPC205501
0.8452	Intermediate Similarity	NPC260781
0.8452	Intermediate Similarity	NPC9933
0.8452	Intermediate Similarity	NPC182368
0.8452	Intermediate Similarity	NPC158784
0.8452	Intermediate Similarity	NPC469706
0.8452	Intermediate Similarity	NPC145979
0.8452	Intermediate Similarity	NPC118000
0.8452	Intermediate Similarity	NPC185955
0.8452	Intermediate Similarity	NPC225815
0.8446	Intermediate Similarity	NPC472800
0.8442	Intermediate Similarity	NPC212142
0.8435	Intermediate Similarity	NPC97834
0.8435	Intermediate Similarity	NPC225696
0.8435	Intermediate Similarity	NPC223008
0.8435	Intermediate Similarity	NPC198154
0.8435	Intermediate Similarity	NPC296915
0.8435	Intermediate Similarity	NPC115335
0.8435	Intermediate Similarity	NPC473107
0.8431	Intermediate Similarity	NPC475872
0.8425	Intermediate Similarity	NPC13005
0.8425	Intermediate Similarity	NPC472798
0.8425	Intermediate Similarity	NPC321086
0.8421	Intermediate Similarity	NPC36732
0.8421	Intermediate Similarity	NPC473845
0.8414	Intermediate Similarity	NPC470225
0.8414	Intermediate Similarity	NPC196193
0.8414	Intermediate Similarity	NPC27187
0.8408	Intermediate Similarity	NPC475227
0.8408	Intermediate Similarity	NPC200645
0.8408	Intermediate Similarity	NPC106669
0.8397	Intermediate Similarity	NPC2745
0.8397	Intermediate Similarity	NPC302915
0.8395	Intermediate Similarity	NPC25889
0.8367	Intermediate Similarity	NPC469610
0.8366	Intermediate Similarity	NPC472457
0.8366	Intermediate Similarity	NPC469557
0.8366	Intermediate Similarity	NPC108994
0.8366	Intermediate Similarity	NPC106126
0.8356	Intermediate Similarity	NPC196765
0.8356	Intermediate Similarity	NPC207892
0.8356	Intermediate Similarity	NPC129784
0.8356	Intermediate Similarity	NPC12875
0.8356	Intermediate Similarity	NPC150011
0.8356	Intermediate Similarity	NPC206224
0.8356	Intermediate Similarity	NPC129106
0.8356	Intermediate Similarity	NPC236014
0.8356	Intermediate Similarity	NPC268917
0.8356	Intermediate Similarity	NPC17343
0.8356	Intermediate Similarity	NPC160623
0.8356	Intermediate Similarity	NPC164574
0.8356	Intermediate Similarity	NPC476166
0.8356	Intermediate Similarity	NPC228369
0.8356	Intermediate Similarity	NPC280653
0.8356	Intermediate Similarity	NPC118114
0.8356	Intermediate Similarity	NPC300875
0.8345	Intermediate Similarity	NPC472797
0.8344	Intermediate Similarity	NPC160196
0.8344	Intermediate Similarity	NPC474442
0.8344	Intermediate Similarity	NPC210192
0.8344	Intermediate Similarity	NPC21902
0.8344	Intermediate Similarity	NPC138149
0.8344	Intermediate Similarity	NPC157783
0.8344	Intermediate Similarity	NPC325860
0.8333	Intermediate Similarity	NPC195561
0.8333	Intermediate Similarity	NPC108164
0.8323	Intermediate Similarity	NPC71726
0.8323	Intermediate Similarity	NPC270751
0.8323	Intermediate Similarity	NPC169510
0.8323	Intermediate Similarity	NPC179809
0.8322	Intermediate Similarity	NPC126101
0.8322	Intermediate Similarity	NPC327735
0.8322	Intermediate Similarity	NPC141717
0.8312	Intermediate Similarity	NPC74320
0.8312	Intermediate Similarity	NPC107120
0.8301	Intermediate Similarity	NPC133251
0.8301	Intermediate Similarity	NPC164183
0.8301	Intermediate Similarity	NPC96447
0.8299	Intermediate Similarity	NPC469611
0.8293	Intermediate Similarity	NPC125465
0.8291	Intermediate Similarity	NPC469699
0.8289	Intermediate Similarity	NPC93640
0.8289	Intermediate Similarity	NPC20631
0.8289	Intermediate Similarity	NPC472353
0.8288	Intermediate Similarity	NPC249425
0.8282	Intermediate Similarity	NPC14294
0.8282	Intermediate Similarity	NPC116759
0.8278	Intermediate Similarity	NPC473049
0.8278	Intermediate Similarity	NPC472794
0.8276	Intermediate Similarity	NPC223912
0.8272	Intermediate Similarity	NPC152424
0.8272	Intermediate Similarity	NPC115624
0.8272	Intermediate Similarity	NPC100465
0.8269	Intermediate Similarity	NPC44452
0.8267	Intermediate Similarity	NPC134260
0.8267	Intermediate Similarity	NPC306365
0.8264	Intermediate Similarity	NPC100414
0.8264	Intermediate Similarity	NPC43000
0.8261	Intermediate Similarity	NPC173726
0.8261	Intermediate Similarity	NPC241600
0.8261	Intermediate Similarity	NPC478269
0.8258	Intermediate Similarity	NPC116019
0.8258	Intermediate Similarity	NPC296377
0.8255	Intermediate Similarity	NPC15109
0.8255	Intermediate Similarity	NPC11727
0.8255	Intermediate Similarity	NPC125579
0.8253	Intermediate Similarity	NPC477573
0.8253	Intermediate Similarity	NPC477572
0.8253	Intermediate Similarity	NPC477571
0.8253	Intermediate Similarity	NPC298778
0.8247	Intermediate Similarity	NPC101255
0.8247	Intermediate Similarity	NPC43716
0.8247	Intermediate Similarity	NPC180953
0.8247	Intermediate Similarity	NPC475719
0.8243	Intermediate Similarity	NPC215037
0.8243	Intermediate Similarity	NPC85435
0.8242	Intermediate Similarity	NPC185498
0.8239	Intermediate Similarity	NPC188578
0.8239	Intermediate Similarity	NPC80918
0.8239	Intermediate Similarity	NPC159922
0.8239	Intermediate Similarity	NPC473425
0.8235	Intermediate Similarity	NPC472451
0.8231	Intermediate Similarity	NPC118683
0.8231	Intermediate Similarity	NPC8899
0.8231	Intermediate Similarity	NPC472590
0.8231	Intermediate Similarity	NPC68205
0.8231	Intermediate Similarity	NPC293203
0.8231	Intermediate Similarity	NPC244888
0.8231	Intermediate Similarity	NPC211413
0.8231	Intermediate Similarity	NPC164804
0.8228	Intermediate Similarity	NPC471154
0.8224	Intermediate Similarity	NPC108674
0.8224	Intermediate Similarity	NPC265075
0.8219	Intermediate Similarity	NPC222108
0.8219	Intermediate Similarity	NPC93962
0.8219	Intermediate Similarity	NPC472795
0.8219	Intermediate Similarity	NPC96719
0.8219	Intermediate Similarity	NPC472796
0.8214	Intermediate Similarity	NPC474345
0.8212	Intermediate Similarity	NPC475836
0.821	Intermediate Similarity	NPC119910
0.8207	Intermediate Similarity	NPC186889
0.8207	Intermediate Similarity	NPC473134
0.8205	Intermediate Similarity	NPC316676
0.8205	Intermediate Similarity	NPC325720
0.8205	Intermediate Similarity	NPC473876
0.82	Intermediate Similarity	NPC262585
0.82	Intermediate Similarity	NPC18189
0.82	Intermediate Similarity	NPC20829
0.8199	Intermediate Similarity	NPC207584
0.8199	Intermediate Similarity	NPC19947
0.8194	Intermediate Similarity	NPC233980
0.8194	Intermediate Similarity	NPC293801
0.8194	Intermediate Similarity	NPC124030
0.8194	Intermediate Similarity	NPC14468

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 NPC476452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	927
0.2-0.3	1763
0.3-0.4	2646
0.4-0.5	1940
0.5-0.6	981
0.6-0.7	509
0.7-0.8	94
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8288	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7228	Approved
0.8224	Intermediate Similarity	NPD6674	Discontinued
0.8176	Intermediate Similarity	NPD37	Approved
0.817	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6234	Discontinued
0.8137	Intermediate Similarity	NPD4967	Phase 2
0.8137	Intermediate Similarity	NPD4965	Approved
0.8137	Intermediate Similarity	NPD4966	Approved
0.8095	Intermediate Similarity	NPD4625	Phase 3
0.8027	Intermediate Similarity	NPD4908	Phase 1
0.8026	Intermediate Similarity	NPD6099	Approved
0.8026	Intermediate Similarity	NPD6100	Approved
0.7931	Intermediate Similarity	NPD4749	Approved
0.7881	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD5124	Phase 1
0.7877	Intermediate Similarity	NPD6696	Suspended
0.7848	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7240	Approved
0.7815	Intermediate Similarity	NPD4140	Approved
0.777	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6559	Discontinued
0.7725	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD4060	Phase 1
0.7679	Intermediate Similarity	NPD7229	Phase 3
0.7671	Intermediate Similarity	NPD1610	Phase 2
0.7661	Intermediate Similarity	NPD5844	Phase 1
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD6959	Discontinued
0.76	Intermediate Similarity	NPD2861	Phase 2
0.7593	Intermediate Similarity	NPD1653	Approved
0.7576	Intermediate Similarity	NPD8455	Phase 2
0.7576	Intermediate Similarity	NPD7819	Suspended
0.7548	Intermediate Similarity	NPD7097	Phase 1
0.7543	Intermediate Similarity	NPD8312	Approved
0.7543	Intermediate Similarity	NPD8313	Approved
0.7532	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5762	Approved
0.7516	Intermediate Similarity	NPD5763	Approved
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5327	Phase 3
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5735	Approved
0.7415	Intermediate Similarity	NPD4626	Approved
0.7391	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7768	Phase 2
0.7381	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3750	Approved
0.7372	Intermediate Similarity	NPD4097	Suspended
0.7372	Intermediate Similarity	NPD6353	Approved
0.7368	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5736	Approved
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5691	Approved
0.7341	Intermediate Similarity	NPD7473	Discontinued
0.7338	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD1091	Approved
0.7314	Intermediate Similarity	NPD7074	Phase 3
0.7303	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7266	Discontinued
0.729	Intermediate Similarity	NPD8032	Phase 2
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7273	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7262	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7340	Approved
0.7257	Intermediate Similarity	NPD7054	Approved
0.7256	Intermediate Similarity	NPD6273	Approved
0.725	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7411	Suspended
0.7235	Intermediate Similarity	NPD7075	Discontinued
0.7235	Intermediate Similarity	NPD3749	Approved
0.7234	Intermediate Similarity	NPD7680	Approved
0.7216	Intermediate Similarity	NPD7472	Approved
0.7211	Intermediate Similarity	NPD7644	Approved
0.7209	Intermediate Similarity	NPD8127	Discontinued
0.72	Intermediate Similarity	NPD3818	Discontinued
0.72	Intermediate Similarity	NPD1611	Approved
0.72	Intermediate Similarity	NPD3705	Approved
0.7188	Intermediate Similarity	NPD6005	Phase 3
0.7188	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6002	Phase 3
0.7188	Intermediate Similarity	NPD6004	Phase 3
0.7181	Intermediate Similarity	NPD1778	Approved
0.7179	Intermediate Similarity	NPD6663	Approved
0.7178	Intermediate Similarity	NPD5058	Phase 3
0.717	Intermediate Similarity	NPD4108	Discontinued
0.7168	Intermediate Similarity	NPD5710	Approved
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.7168	Intermediate Similarity	NPD5711	Approved
0.7161	Intermediate Similarity	NPD3027	Phase 3
0.716	Intermediate Similarity	NPD7466	Approved
0.716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7003	Approved
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD3620	Phase 2
0.7134	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7985	Registered
0.7107	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1652	Phase 2
0.7095	Intermediate Similarity	NPD7808	Phase 3
0.7095	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7447	Phase 1
0.7091	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6797	Phase 2
0.7078	Intermediate Similarity	NPD4624	Approved
0.7075	Intermediate Similarity	NPD6671	Approved
0.7067	Intermediate Similarity	NPD5126	Approved
0.7067	Intermediate Similarity	NPD5125	Phase 3
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD3748	Approved
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD8651	Approved
0.7059	Intermediate Similarity	NPD1283	Approved
0.7055	Intermediate Similarity	NPD4628	Phase 3
0.7055	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1398	Phase 1
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7052	Intermediate Similarity	NPD5494	Approved
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.703	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7213	Phase 3
0.703	Intermediate Similarity	NPD7041	Phase 2
0.703	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7212	Phase 2
0.7025	Intermediate Similarity	NPD2979	Phase 3
0.7024	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3226	Approved
0.702	Intermediate Similarity	NPD3496	Discontinued
0.7013	Intermediate Similarity	NPD3094	Phase 2
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD1934	Approved
0.6995	Remote Similarity	NPD7906	Approved
0.6994	Remote Similarity	NPD2800	Approved
0.6994	Remote Similarity	NPD5709	Phase 3
0.6994	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4481	Phase 3
0.6988	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4380	Phase 2
0.6982	Remote Similarity	NPD6599	Discontinued
0.6975	Remote Similarity	NPD2346	Discontinued
0.6975	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6667	Approved
0.697	Remote Similarity	NPD6666	Approved
0.6961	Remote Similarity	NPD7313	Approved
0.6961	Remote Similarity	NPD7310	Approved
0.6961	Remote Similarity	NPD7311	Approved
0.6961	Remote Similarity	NPD7312	Approved
0.6961	Remote Similarity	NPD4577	Approved
0.6961	Remote Similarity	NPD4578	Approved
0.6959	Remote Similarity	NPD1465	Phase 2
0.6959	Remote Similarity	NPD5929	Approved
0.6957	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4666	Phase 3
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD3892	Phase 2
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4663	Approved
0.6933	Remote Similarity	NPD7037	Approved
0.6933	Remote Similarity	NPD1549	Phase 2
0.6933	Remote Similarity	NPD7741	Discontinued
0.6933	Remote Similarity	NPD3091	Approved
0.6928	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7309	Approved
0.6914	Remote Similarity	NPD1551	Phase 2
0.6914	Remote Similarity	NPD2438	Suspended
0.6914	Remote Similarity	NPD2935	Discontinued
0.6911	Remote Similarity	NPD6823	Phase 2
0.6905	Remote Similarity	NPD4727	Phase 1
0.6905	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2797	Approved
0.6899	Remote Similarity	NPD6798	Discontinued
0.6897	Remote Similarity	NPD4750	Phase 3
0.6895	Remote Similarity	NPD6777	Approved
0.6895	Remote Similarity	NPD6781	Approved
0.6895	Remote Similarity	NPD6782	Approved
0.6895	Remote Similarity	NPD6780	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