NPASS Compound

Structure

NPC472394 OpenBabel07101718202D 42 45 0 0 1 0 0 0 0 0999 V2000 -0.5924 1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 -2.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4397 -2.9401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4187 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5603 0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8642 -0.5104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5222 -1.4501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5149 -2.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6489 -2.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5149 -1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7829 -2.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6489 -0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 0.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1736 -0.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 -1.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4397 -2.9401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5209 2.2704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0603 1.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7829 -1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1133 -1.3268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 -0.6840 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7057 0.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.6840 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4397 -1.2080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1133 0.6428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4397 0.5240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9168 -0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8794 -0.6840 0.0000 C 0 0 0 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 0.0603 -3.8061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6946 3.2552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5603 2.2561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9397 0.3420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9168 0.3160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 -2.0741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2870 1.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 1.3900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0508 -1.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 2 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 32 1 0 0 0 0 7 32 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 33 1 0 0 0 0 16 24 1 0 0 0 0 17 24 1 0 0 0 0 17 26 2 0 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 34 2 0 0 0 0 19 39 1 0 0 0 0 20 35 2 0 0 0 0 20 40 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 31 1 0 0 0 0 23 16 1 6 0 0 0 23 28 1 0 0 0 0 23 32 1 0 0 0 0 24 37 2 0 0 0 0 25 42 1 6 0 0 0 26 29 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 33 1 1 0 0 0 28 39 1 6 0 0 0 29 30 1 0 0 0 0 29 40 1 1 0 0 0 30 33 1 6 0 0 0 30 41 1 0 0 0 0 31 38 2 0 0 0 0 31 42 1 0 0 0 0 33 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.27
Volume:	597.846
LogP:	4.257
LogD:	3.286
LogS:	-4.554
# Rotatable Bonds:	9
TPSA:	122.27
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	5.339
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.938
MDCK Permeability:	4.926291876472533e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	79.61872863769531%
Volume Distribution (VD):	1.72
Pgp-substrate:	19.056684494018555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.521
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.713
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	3.237
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.965
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.82
Maximum Recommended Daily Dose:	0.574
Skin Sensitization:	0.083
Carcinogencity:	0.122
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC472394

Natural Product ID:	NPC472394
*Common Name:**	KCVBKOGPGLTLNX-KQDCEKGYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KCVBKOGPGLTLNX-KQDCEKGYSA-N
Standard InCHI:	InChI=1S/C33H40O9/c1-17-24(37)16-23-28(39-19(3)34)27-18(2)25(42-31(38)22-12-10-9-11-13-22)14-15-33(27,8)30(41-21(5)36)29(40-20(4)35)26(17)32(23,6)7/h9-13,23,25,27-30H,2,14-16H2,1,3-8H3/t23-,25-,27-,28+,29+,30-,33+/m0/s1
SMILES:	CC1=C2C(C(C3(CCC(C(=C)C3C(C(C2(C)C)CC1=O)OC(=O)C)OC(=O)C4=CC=CC=C4)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL339923
PubChem CID:	15378568
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Control	=	184.0	%	PMID[559295]
NPT2	Others	Unspecified	Control	=	645.0	%	PMID[559295]
NPT2	Others	Unspecified	Activity	=	87.0	%	PMID[559296]

☑ 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 NPC472394 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	320
0.1-0.2	1173
0.2-0.3	2276
0.3-0.4	5421
0.4-0.5	10334
0.5-0.6	12219
0.6-0.7	9694
0.7-0.8	1097
0.8-0.85	131
0.85-0.9	20
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9538	High Similarity	NPC472371
0.9538	High Similarity	NPC472395
0.9385	High Similarity	NPC472374
0.9385	High Similarity	NPC472372
0.9375	High Similarity	NPC471880
0.9355	High Similarity	NPC469742
0.9318	High Similarity	NPC475400
0.9213	High Similarity	NPC195224
0.9141	High Similarity	NPC225103
0.9134	High Similarity	NPC473423
0.907	High Similarity	NPC473443
0.907	High Similarity	NPC472388
0.9037	High Similarity	NPC34012
0.9	High Similarity	NPC472418
0.9	High Similarity	NPC472361
0.8931	High Similarity	NPC209851
0.8897	High Similarity	NPC475135
0.8889	High Similarity	NPC477904
0.8889	High Similarity	NPC183270
0.8872	High Similarity	NPC66761
0.8872	High Similarity	NPC472577
0.8872	High Similarity	NPC291638
0.8872	High Similarity	NPC17877
0.8872	High Similarity	NPC473216
0.8872	High Similarity	NPC473399
0.8872	High Similarity	NPC195647
0.8864	High Similarity	NPC472437
0.8849	High Similarity	NPC217918
0.8797	High Similarity	NPC474608
0.8788	High Similarity	NPC475493
0.8788	High Similarity	NPC80599
0.8779	High Similarity	NPC147561
0.8777	High Similarity	NPC474935
0.8768	High Similarity	NPC38696
0.875	High Similarity	NPC473109
0.875	High Similarity	NPC200592
0.875	High Similarity	NPC473758
0.875	High Similarity	NPC147880
0.875	High Similarity	NPC473085
0.875	High Similarity	NPC472547
0.875	High Similarity	NPC476094
0.875	High Similarity	NPC473112
0.875	High Similarity	NPC184747
0.875	High Similarity	NPC473060
0.875	High Similarity	NPC211137
0.875	High Similarity	NPC43241
0.875	High Similarity	NPC48017
0.875	High Similarity	NPC473081
0.875	High Similarity	NPC4341
0.875	High Similarity	NPC473613
0.8731	High Similarity	NPC477893
0.8723	High Similarity	NPC91730
0.872	High Similarity	NPC89324
0.8686	High Similarity	NPC16912
0.8676	High Similarity	NPC475652
0.8676	High Similarity	NPC210591
0.8676	High Similarity	NPC214550
0.8667	High Similarity	NPC472545
0.8667	High Similarity	NPC472551
0.8662	High Similarity	NPC197037
0.8661	High Similarity	NPC473439
0.8661	High Similarity	NPC300827
0.8633	High Similarity	NPC470231
0.8623	High Similarity	NPC472546
0.8613	High Similarity	NPC97667
0.8613	High Similarity	NPC90614
0.8613	High Similarity	NPC171207
0.8603	High Similarity	NPC183122
0.8603	High Similarity	NPC39549
0.8603	High Similarity	NPC283375
0.8603	High Similarity	NPC475373
0.8594	High Similarity	NPC473749
0.8593	High Similarity	NPC477896
0.8583	High Similarity	NPC473243
0.8571	High Similarity	NPC471100
0.8571	High Similarity	NPC471107
0.8571	High Similarity	NPC127857
0.8561	High Similarity	NPC270498
0.8561	High Similarity	NPC177340
0.8561	High Similarity	NPC475429
0.8561	High Similarity	NPC191082
0.8561	High Similarity	NPC139067
0.8561	High Similarity	NPC147217
0.8561	High Similarity	NPC477894
0.8561	High Similarity	NPC246480
0.8561	High Similarity	NPC473673
0.8551	High Similarity	NPC27377
0.8551	High Similarity	NPC291599
0.8551	High Similarity	NPC41481
0.8551	High Similarity	NPC472576
0.8551	High Similarity	NPC224491
0.8551	High Similarity	NPC118080
0.8551	High Similarity	NPC87448
0.8551	High Similarity	NPC97947
0.855	High Similarity	NPC169913
0.8542	High Similarity	NPC248265
0.8542	High Similarity	NPC219419
0.8542	High Similarity	NPC11588
0.8542	High Similarity	NPC229545
0.8542	High Similarity	NPC134685
0.8527	High Similarity	NPC12016
0.8519	High Similarity	NPC48929
0.8519	High Similarity	NPC203486
0.85	High Similarity	NPC70716
0.85	High Similarity	NPC472569
0.85	High Similarity	NPC125106
0.85	High Similarity	NPC472573
0.85	High Similarity	NPC163719
0.85	High Similarity	NPC67777
0.85	High Similarity	NPC25768
0.85	High Similarity	NPC476974
0.85	High Similarity	NPC57628
0.85	High Similarity	NPC11685
0.85	High Similarity	NPC95265
0.85	High Similarity	NPC472570
0.85	High Similarity	NPC95810
0.85	High Similarity	NPC51314
0.85	High Similarity	NPC188865
0.8489	Intermediate Similarity	NPC182869
0.8483	Intermediate Similarity	NPC114357
0.8483	Intermediate Similarity	NPC155329
0.8483	Intermediate Similarity	NPC259144
0.8483	Intermediate Similarity	NPC21410
0.8483	Intermediate Similarity	NPC473670
0.8478	Intermediate Similarity	NPC275592
0.8478	Intermediate Similarity	NPC100913
0.8473	Intermediate Similarity	NPC275576
0.8467	Intermediate Similarity	NPC184109
0.8462	Intermediate Similarity	NPC254558
0.8462	Intermediate Similarity	NPC7095
0.8462	Intermediate Similarity	NPC472373
0.8462	Intermediate Similarity	NPC112216
0.844	Intermediate Similarity	NPC469349
0.844	Intermediate Similarity	NPC476973
0.844	Intermediate Similarity	NPC470157
0.844	Intermediate Similarity	NPC472572
0.844	Intermediate Similarity	NPC177940
0.844	Intermediate Similarity	NPC471104
0.844	Intermediate Similarity	NPC472556
0.844	Intermediate Similarity	NPC200471
0.844	Intermediate Similarity	NPC472571
0.844	Intermediate Similarity	NPC472568
0.844	Intermediate Similarity	NPC470159
0.844	Intermediate Similarity	NPC174982
0.844	Intermediate Similarity	NPC70403
0.844	Intermediate Similarity	NPC158663
0.844	Intermediate Similarity	NPC171525
0.844	Intermediate Similarity	NPC96903
0.844	Intermediate Similarity	NPC472575
0.844	Intermediate Similarity	NPC184817
0.844	Intermediate Similarity	NPC473088
0.844	Intermediate Similarity	NPC29704
0.8433	Intermediate Similarity	NPC470278
0.8429	Intermediate Similarity	NPC163087
0.8429	Intermediate Similarity	NPC131966
0.8429	Intermediate Similarity	NPC95449
0.8429	Intermediate Similarity	NPC191387
0.8425	Intermediate Similarity	NPC217091
0.8417	Intermediate Similarity	NPC266374
0.8409	Intermediate Similarity	NPC473220
0.8409	Intermediate Similarity	NPC470753
0.8403	Intermediate Similarity	NPC51602
0.8403	Intermediate Similarity	NPC101043
0.8403	Intermediate Similarity	NPC306799
0.8397	Intermediate Similarity	NPC471758
0.8392	Intermediate Similarity	NPC81698
0.8392	Intermediate Similarity	NPC250046
0.8392	Intermediate Similarity	NPC60509
0.8382	Intermediate Similarity	NPC471911
0.8382	Intermediate Similarity	NPC153617
0.8382	Intermediate Similarity	NPC4242
0.8382	Intermediate Similarity	NPC329913
0.838	Intermediate Similarity	NPC473602
0.8372	Intermediate Similarity	NPC50872
0.837	Intermediate Similarity	NPC238370
0.8369	Intermediate Similarity	NPC241951
0.8369	Intermediate Similarity	NPC475759
0.8369	Intermediate Similarity	NPC470152
0.8369	Intermediate Similarity	NPC475122
0.8367	Intermediate Similarity	NPC472393
0.8357	Intermediate Similarity	NPC192658
0.8345	Intermediate Similarity	NPC87934
0.8345	Intermediate Similarity	NPC162613
0.8345	Intermediate Similarity	NPC472548
0.8333	Intermediate Similarity	NPC327511
0.8333	Intermediate Similarity	NPC161239
0.8333	Intermediate Similarity	NPC473214
0.8333	Intermediate Similarity	NPC470245
0.8333	Intermediate Similarity	NPC470765
0.8333	Intermediate Similarity	NPC45821
0.8333	Intermediate Similarity	NPC205305
0.8333	Intermediate Similarity	NPC476599
0.8333	Intermediate Similarity	NPC165260
0.8333	Intermediate Similarity	NPC198455
0.8322	Intermediate Similarity	NPC281717
0.8309	Intermediate Similarity	NPC472656
0.8298	Intermediate Similarity	NPC477468
0.8296	Intermediate Similarity	NPC475478
0.8288	Intermediate Similarity	NPC257213
0.8288	Intermediate Similarity	NPC1173

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 NPC472394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	803
0.2-0.3	1367
0.3-0.4	2817
0.4-0.5	2270
0.5-0.6	1254
0.6-0.7	340
0.7-0.8	25
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
0.7879	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7236	Approved
0.7795	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2182	Approved
0.7702	Intermediate Similarity	NPD8368	Discontinued
0.7667	Intermediate Similarity	NPD7239	Suspended
0.7625	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7799	Discontinued
0.7561	Intermediate Similarity	NPD8407	Phase 2
0.75	Intermediate Similarity	NPD6287	Discontinued
0.747	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD164	Approved
0.7447	Intermediate Similarity	NPD7008	Discontinued
0.7432	Intermediate Similarity	NPD8166	Discontinued
0.7432	Intermediate Similarity	NPD4628	Phase 3
0.7426	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD2629	Approved
0.7405	Intermediate Similarity	NPD7094	Approved
0.7405	Intermediate Similarity	NPD6858	Approved
0.7381	Intermediate Similarity	NPD8361	Approved
0.7381	Intermediate Similarity	NPD8360	Approved
0.7381	Intermediate Similarity	NPD8435	Approved
0.7364	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7961	Discontinued
0.7328	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5951	Approved
0.728	Intermediate Similarity	NPD1238	Approved
0.7239	Intermediate Similarity	NPD4198	Discontinued
0.7234	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7058	Phase 2
0.7215	Intermediate Similarity	NPD7057	Phase 3
0.7176	Intermediate Similarity	NPD2067	Discontinued
0.7153	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD8485	Approved
0.7103	Intermediate Similarity	NPD8032	Phase 2
0.7103	Intermediate Similarity	NPD7713	Phase 3
0.7101	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7819	Suspended
0.7078	Intermediate Similarity	NPD6273	Approved
0.7055	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7458	Discontinued
0.7047	Intermediate Similarity	NPD2438	Suspended
0.7019	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2346	Discontinued
0.6992	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3748	Approved
0.698	Remote Similarity	NPD7305	Phase 1
0.6977	Remote Similarity	NPD1929	Approved
0.6977	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1930	Approved
0.6959	Remote Similarity	NPD8150	Discontinued
0.6957	Remote Similarity	NPD7741	Discontinued
0.695	Remote Similarity	NPD3972	Approved
0.6943	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3226	Approved
0.6939	Remote Similarity	NPD2979	Phase 3
0.6912	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6599	Discontinued
0.6882	Remote Similarity	NPD8312	Approved
0.6882	Remote Similarity	NPD8313	Approved
0.6879	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7798	Approved
0.6875	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2066	Phase 3
0.6871	Remote Similarity	NPD6663	Approved
0.6867	Remote Similarity	NPD2799	Discontinued
0.6867	Remote Similarity	NPD7473	Discontinued
0.6863	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7003	Approved
0.6857	Remote Similarity	NPD5125	Phase 3
0.6857	Remote Similarity	NPD5126	Approved
0.6852	Remote Similarity	NPD7075	Discontinued
0.685	Remote Similarity	NPD3495	Discontinued
0.6835	Remote Similarity	NPD9545	Approved
0.6828	Remote Similarity	NPD5736	Approved
0.6815	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2313	Discontinued
0.6802	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5909	Discontinued
0.6781	Remote Similarity	NPD6832	Phase 2
0.6776	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1989	Approved
0.6768	Remote Similarity	NPD5494	Approved
0.6765	Remote Similarity	NPD6764	Approved
0.6765	Remote Similarity	NPD6765	Approved
0.6763	Remote Similarity	NPD7610	Discontinued
0.6761	Remote Similarity	NPD1281	Approved
0.6753	Remote Similarity	NPD3750	Approved
0.675	Remote Similarity	NPD6386	Approved
0.675	Remote Similarity	NPD6385	Approved
0.6746	Remote Similarity	NPD1202	Approved
0.6738	Remote Similarity	NPD17	Approved
0.6736	Remote Similarity	NPD1876	Approved
0.6736	Remote Similarity	NPD5667	Approved
0.6735	Remote Similarity	NPD6039	Approved
0.6728	Remote Similarity	NPD5402	Approved
0.6718	Remote Similarity	NPD6647	Phase 2
0.6713	Remote Similarity	NPD6637	Approved
0.6711	Remote Similarity	NPD2796	Approved
0.671	Remote Similarity	NPD6190	Approved
0.6708	Remote Similarity	NPD37	Approved
0.6708	Remote Similarity	NPD6801	Discontinued
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4380	Phase 2
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD6232	Discontinued
0.6687	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD7631	Approved
0.6667	Remote Similarity	NPD1237	Approved
0.6646	Remote Similarity	NPD6873	Phase 2
0.6645	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4110	Phase 3
0.6644	Remote Similarity	NPD6085	Phase 2
0.6644	Remote Similarity	NPD2798	Approved
0.6644	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1932	Approved
0.6626	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3817	Phase 2
0.6625	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6799	Approved
0.6621	Remote Similarity	NPD2198	Approved
0.6621	Remote Similarity	NPD1283	Approved
0.6621	Remote Similarity	NPD2199	Approved
0.662	Remote Similarity	NPD2932	Approved
0.6614	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6784	Approved
0.6609	Remote Similarity	NPD6785	Approved
0.6606	Remote Similarity	NPD6234	Discontinued
0.6604	Remote Similarity	NPD5403	Approved
0.6603	Remote Similarity	NPD3887	Approved
0.6601	Remote Similarity	NPD2531	Phase 2
0.6601	Remote Similarity	NPD2935	Discontinued
0.6597	Remote Similarity	NPD1608	Approved
0.6596	Remote Similarity	NPD8462	Phase 1
0.6594	Remote Similarity	NPD1241	Discontinued
0.6594	Remote Similarity	NPD6010	Discontinued
0.6593	Remote Similarity	NPD2329	Discontinued
0.6587	Remote Similarity	NPD7609	Phase 3
0.6585	Remote Similarity	NPD7768	Phase 2
0.6582	Remote Similarity	NPD2533	Approved
0.6582	Remote Similarity	NPD2534	Approved
0.6582	Remote Similarity	NPD5401	Approved
0.6582	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2532	Approved
0.6582	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7097	Phase 1
0.6575	Remote Similarity	NPD1470	Approved
0.6573	Remote Similarity	NPD3023	Approved
0.6573	Remote Similarity	NPD3026	Approved
0.657	Remote Similarity	NPD7685	Pre-registration
0.6564	Remote Similarity	NPD8455	Phase 2
0.6564	Remote Similarity	NPD5761	Phase 2
0.6564	Remote Similarity	NPD5760	Phase 2
0.6558	Remote Similarity	NPD7266	Discontinued
0.6554	Remote Similarity	NPD7055	Discontinued
0.6549	Remote Similarity	NPD5691	Approved
0.6549	Remote Similarity	NPD1651	Approved
0.6543	Remote Similarity	NPD7411	Suspended
0.6541	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7714	Approved
0.6533	Remote Similarity	NPD7715	Approved
0.6529	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4806	Approved
0.6528	Remote Similarity	NPD4807	Approved
0.6528	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5353	Approved
0.6519	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7095	Approved
0.6503	Remote Similarity	NPD5306	Approved
0.6503	Remote Similarity	NPD3019	Approved
0.6503	Remote Similarity	NPD5305	Approved
0.65	Remote Similarity	NPD3317	Approved
0.6497	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5404	Approved
0.6494	Remote Similarity	NPD5405	Approved
0.6494	Remote Similarity	NPD5408	Approved
0.6494	Remote Similarity	NPD5406	Approved
0.649	Remote Similarity	NPD4140	Approved
0.649	Remote Similarity	NPD4307	Phase 2
0.6483	Remote Similarity	NPD4878	Approved
0.6481	Remote Similarity	NPD7028	Phase 2
0.6479	Remote Similarity	NPD7009	Phase 2
0.6478	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6559	Discontinued
0.6471	Remote Similarity	NPD2569	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