NPASS Compound

Structure

NPC470030 OpenBabel07101719162D 39 46 0 0 1 0 0 0 0 0999 V2000 2.6701 0.6475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0382 0.1159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4042 -5.2501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4042 -5.2501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8468 -3.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8468 -0.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0229 -0.8618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1722 -4.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3061 -3.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7702 -2.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9042 -2.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4890 -2.6931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1722 -1.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0382 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -0.1615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1722 0.6159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 -1.8841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0382 -3.8841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3061 -2.8841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7702 -3.8841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3061 -0.8841 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4890 -1.0751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9042 -4.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4401 -2.3841 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4401 -1.3841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0382 -2.8841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1722 -2.3841 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1722 1.6159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6363 -4.3841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3061 0.1159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9067 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -2.1970 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 2 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 30 1 0 0 0 0 12 16 1 0 0 0 0 13 27 1 0 0 0 0 14 22 1 0 0 0 0 15 30 1 0 0 0 0 15 31 1 0 0 0 0 16 1 1 1 0 0 0 16 23 1 0 0 0 0 17 33 2 0 0 0 0 17 36 1 0 0 0 0 18 13 1 6 0 0 0 18 23 1 0 0 0 0 18 37 1 0 0 0 0 19 26 1 0 0 0 0 19 30 1 6 0 0 0 20 27 1 1 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 34 1 6 0 0 0 22 28 1 6 0 0 0 22 36 1 0 0 0 0 23 28 1 6 0 0 0 24 29 1 6 0 0 0 24 32 1 0 0 0 0 24 38 1 0 0 0 0 25 29 1 1 0 0 0 25 35 1 0 0 0 0 25 39 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 1 0 0 0 29 38 1 0 0 0 0 30 31 1 1 0 0 0 31 14 1 1 0 0 0 32 12 1 6 0 0 0 32 37 1 0 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.34
Volume:	552.471
LogP:	4.488
LogD:	3.965
LogS:	-4.823
# Rotatable Bonds:	2
TPSA:	97.75
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	6.736
Fsp3:	0.969
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:	-5.243
MDCK Permeability:	2.8989403290324844e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.546

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421
Plasma Protein Binding (PPB):	85.83850860595703%
Volume Distribution (VD):	1.458
Pgp-substrate:	13.52099895477295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.397
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.823
CYP2C9-inhibitor:	0.205
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	4.025
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.588
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.533
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.904
Carcinogencity:	0.187
Eye Corrosion:	0.03
Eye Irritation:	0.066
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC470030

Natural Product ID:	NPC470030
*Common Name:**	NRWLZMLCGSBEEU-HIMBUXHBSA-N
IUPAC Name:	n.a.
Synonyms:	12-O-Acetylacteol
Standard InCHIKey:	NRWLZMLCGSBEEU-HIMBUXHBSA-N
Standard InCHI:	InChI=1S/C32H48O7/c1-16-12-32(24-29(7,38-24)25(35)39-32)37-18-13-27(5)20-9-8-19-26(3,4)21(34)10-11-30(19)15-31(20,30)14-22(36-17(2)33)28(27,6)23(16)18/h16,18-25,34-35H,8-15H2,1-7H3/t16-,18+,19+,20+,21+,22-,23+,24+,25+,27+,28-,29+,30-,31+,32-/m1/s1
SMILES:	CC1CC2(C3C(O3)(C(O2)O)C)OC4C1C5(C(CC67CC68CCC(C(C8CCC7C5(C4)C)(C)C)O)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651285
PubChem CID:	23640137
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[11824572]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124775]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562825]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21082802]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21082802]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO525	Actaea racemosa	Species	Ranunculaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	126.0	%	PMID[551603]

☑ 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 NPC470030 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	546
0.1-0.2	4739
0.2-0.3	13844
0.3-0.4	10222
0.4-0.5	5770
0.5-0.6	4043
0.6-0.7	2460
0.7-0.8	840
0.8-0.85	169
0.85-0.9	35
0.9-0.95	24
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC476837
0.9684	High Similarity	NPC139181
0.9684	High Similarity	NPC97260
0.9474	High Similarity	NPC472081
0.9474	High Similarity	NPC476512
0.9474	High Similarity	NPC108227
0.9462	High Similarity	NPC252056
0.9462	High Similarity	NPC156377
0.9457	High Similarity	NPC30687
0.9375	High Similarity	NPC470029
0.9375	High Similarity	NPC310138
0.9375	High Similarity	NPC114700
0.9375	High Similarity	NPC134967
0.9247	High Similarity	NPC191915
0.9247	High Similarity	NPC151214
0.9247	High Similarity	NPC175
0.9149	High Similarity	NPC473065
0.9149	High Similarity	NPC473067
0.9149	High Similarity	NPC473064
0.9072	High Similarity	NPC476838
0.9072	High Similarity	NPC476839
0.9072	High Similarity	NPC475574
0.9053	High Similarity	NPC142264
0.9053	High Similarity	NPC237071
0.9053	High Similarity	NPC476510
0.9053	High Similarity	NPC203434
0.9053	High Similarity	NPC238796
0.9032	High Similarity	NPC59006
0.8958	High Similarity	NPC233649
0.8958	High Similarity	NPC470028
0.8958	High Similarity	NPC475207
0.8936	High Similarity	NPC311246
0.8936	High Similarity	NPC167644
0.8925	High Similarity	NPC473542
0.8854	High Similarity	NPC296936
0.8842	High Similarity	NPC45959
0.8842	High Similarity	NPC3538
0.8842	High Similarity	NPC252253
0.8842	High Similarity	NPC113500
0.8842	High Similarity	NPC477224
0.883	High Similarity	NPC473066
0.883	High Similarity	NPC149966
0.883	High Similarity	NPC5632
0.8817	High Similarity	NPC228059
0.8817	High Similarity	NPC82955
0.8763	High Similarity	NPC470591
0.875	High Similarity	NPC21897
0.875	High Similarity	NPC94582
0.875	High Similarity	NPC57964
0.8737	High Similarity	NPC144790
0.8737	High Similarity	NPC122083
0.8737	High Similarity	NPC182740
0.8737	High Similarity	NPC473726
0.8737	High Similarity	NPC256104
0.8737	High Similarity	NPC149400
0.8737	High Similarity	NPC88962
0.8737	High Similarity	NPC211845
0.8723	High Similarity	NPC279329
0.871	High Similarity	NPC281004
0.8673	High Similarity	NPC292775
0.866	High Similarity	NPC304011
0.866	High Similarity	NPC139271
0.8646	High Similarity	NPC253268
0.8646	High Similarity	NPC291547
0.8646	High Similarity	NPC179859
0.8646	High Similarity	NPC473774
0.8646	High Similarity	NPC473851
0.8646	High Similarity	NPC131693
0.8646	High Similarity	NPC24960
0.8646	High Similarity	NPC475436
0.8646	High Similarity	NPC174024
0.8646	High Similarity	NPC312678
0.8641	High Similarity	NPC227879
0.8641	High Similarity	NPC208333
0.8632	High Similarity	NPC36372
0.8632	High Similarity	NPC229801
0.8632	High Similarity	NPC293609
0.8632	High Similarity	NPC210759
0.8632	High Similarity	NPC307167
0.8617	High Similarity	NPC102725
0.8617	High Similarity	NPC473472
0.8617	High Similarity	NPC20822
0.8602	High Similarity	NPC43912
0.8602	High Similarity	NPC140446
0.8587	High Similarity	NPC290612
0.8586	High Similarity	NPC41843
0.8571	High Similarity	NPC477222
0.8571	High Similarity	NPC477223
0.8571	High Similarity	NPC210157
0.8557	High Similarity	NPC474399
0.8542	High Similarity	NPC177834
0.8542	High Similarity	NPC141769
0.8542	High Similarity	NPC477547
0.8542	High Similarity	NPC48339
0.8542	High Similarity	NPC297348
0.8542	High Similarity	NPC325828
0.8542	High Similarity	NPC250393
0.8542	High Similarity	NPC249204
0.8542	High Similarity	NPC277774
0.8542	High Similarity	NPC477451
0.8542	High Similarity	NPC234352
0.8526	High Similarity	NPC223143
0.8526	High Similarity	NPC65550
0.8505	High Similarity	NPC212660
0.8495	Intermediate Similarity	NPC215968
0.8495	Intermediate Similarity	NPC471411
0.8495	Intermediate Similarity	NPC471410
0.8495	Intermediate Similarity	NPC155531
0.8485	Intermediate Similarity	NPC473638
0.8478	Intermediate Similarity	NPC474156
0.8469	Intermediate Similarity	NPC121453
0.8454	Intermediate Similarity	NPC309866
0.8454	Intermediate Similarity	NPC222731
0.8454	Intermediate Similarity	NPC217205
0.8454	Intermediate Similarity	NPC305418
0.8454	Intermediate Similarity	NPC291203
0.8454	Intermediate Similarity	NPC264101
0.8454	Intermediate Similarity	NPC294686
0.8454	Intermediate Similarity	NPC473503
0.8454	Intermediate Similarity	NPC471464
0.8438	Intermediate Similarity	NPC476668
0.8438	Intermediate Similarity	NPC473637
0.8438	Intermediate Similarity	NPC473830
0.8438	Intermediate Similarity	NPC204881
0.8421	Intermediate Similarity	NPC131466
0.8404	Intermediate Similarity	NPC161928
0.8404	Intermediate Similarity	NPC210658
0.8387	Intermediate Similarity	NPC232044
0.8387	Intermediate Similarity	NPC273290
0.8384	Intermediate Similarity	NPC307534
0.8384	Intermediate Similarity	NPC476112
0.8384	Intermediate Similarity	NPC274200
0.837	Intermediate Similarity	NPC477285
0.837	Intermediate Similarity	NPC111582
0.8367	Intermediate Similarity	NPC6295
0.8367	Intermediate Similarity	NPC469710
0.8367	Intermediate Similarity	NPC475351
0.8367	Intermediate Similarity	NPC107188
0.8367	Intermediate Similarity	NPC92196
0.8367	Intermediate Similarity	NPC473610
0.8367	Intermediate Similarity	NPC473727
0.8367	Intermediate Similarity	NPC206003
0.8367	Intermediate Similarity	NPC215570
0.8367	Intermediate Similarity	NPC19400
0.8367	Intermediate Similarity	NPC107962
0.8367	Intermediate Similarity	NPC211354
0.8365	Intermediate Similarity	NPC472079
0.8351	Intermediate Similarity	NPC137004
0.8351	Intermediate Similarity	NPC172838
0.8351	Intermediate Similarity	NPC476669
0.8317	Intermediate Similarity	NPC477225
0.8317	Intermediate Similarity	NPC477172
0.8316	Intermediate Similarity	NPC128475
0.8316	Intermediate Similarity	NPC470872
0.8302	Intermediate Similarity	NPC473062
0.83	Intermediate Similarity	NPC473518
0.83	Intermediate Similarity	NPC473616
0.8298	Intermediate Similarity	NPC477283
0.8283	Intermediate Similarity	NPC287483
0.8283	Intermediate Similarity	NPC470866
0.8283	Intermediate Similarity	NPC184617
0.8283	Intermediate Similarity	NPC475643
0.8283	Intermediate Similarity	NPC116756
0.8283	Intermediate Similarity	NPC84111
0.8283	Intermediate Similarity	NPC232037
0.8283	Intermediate Similarity	NPC98018
0.8283	Intermediate Similarity	NPC473287
0.8283	Intermediate Similarity	NPC470863
0.8283	Intermediate Similarity	NPC30856
0.8283	Intermediate Similarity	NPC103616
0.8283	Intermediate Similarity	NPC470864
0.8283	Intermediate Similarity	NPC132080
0.8283	Intermediate Similarity	NPC128572
0.8283	Intermediate Similarity	NPC160426
0.8283	Intermediate Similarity	NPC195297
0.8283	Intermediate Similarity	NPC475625
0.8283	Intermediate Similarity	NPC473601
0.8283	Intermediate Similarity	NPC470865
0.8283	Intermediate Similarity	NPC284104
0.8283	Intermediate Similarity	NPC97700
0.828	Intermediate Similarity	NPC18953
0.828	Intermediate Similarity	NPC227260
0.8265	Intermediate Similarity	NPC475325
0.8261	Intermediate Similarity	NPC470611
0.8261	Intermediate Similarity	NPC477286
0.8261	Intermediate Similarity	NPC296734
0.8261	Intermediate Similarity	NPC286719
0.8261	Intermediate Similarity	NPC475388
0.8224	Intermediate Similarity	NPC477489
0.8211	Intermediate Similarity	NPC472396
0.8211	Intermediate Similarity	NPC5943
0.82	Intermediate Similarity	NPC232611
0.82	Intermediate Similarity	NPC470862
0.82	Intermediate Similarity	NPC51520
0.82	Intermediate Similarity	NPC470861
0.82	Intermediate Similarity	NPC472273
0.82	Intermediate Similarity	NPC303069
0.82	Intermediate Similarity	NPC83137
0.82	Intermediate Similarity	NPC115165
0.8191	Intermediate Similarity	NPC235402

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 NPC470030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	558
0.1-0.2	4448
0.2-0.3	2921
0.3-0.4	660
0.4-0.5	333
0.5-0.6	175
0.6-0.7	39
0.7-0.8	15
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
0.8542	High Similarity	NPD8171	Discontinued
0.8077	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD6928	Phase 2
0.7565	Intermediate Similarity	NPD8294	Approved
0.7565	Intermediate Similarity	NPD8377	Approved
0.7544	Intermediate Similarity	NPD7327	Approved
0.7544	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7478	Intermediate Similarity	NPD7516	Approved
0.7345	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD7991	Discontinued
0.7107	Intermediate Similarity	NPD7507	Approved
0.6992	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7319	Approved
0.6923	Remote Similarity	NPD6940	Discontinued
0.6917	Remote Similarity	NPD7503	Approved
0.6907	Remote Similarity	NPD6114	Approved
0.6907	Remote Similarity	NPD6115	Approved
0.6907	Remote Similarity	NPD6697	Approved
0.6907	Remote Similarity	NPD6118	Approved
0.6842	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6412	Phase 2
0.6804	Remote Similarity	NPD6116	Phase 1
0.6774	Remote Similarity	NPD8293	Discontinued
0.6733	Remote Similarity	NPD3669	Approved
0.6733	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD1811	Approved
0.6667	Remote Similarity	NPD1810	Approved
0.6585	Remote Similarity	NPD6370	Approved
0.6583	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD6616	Approved
0.6429	Remote Similarity	NPD3702	Approved
0.6423	Remote Similarity	NPD6054	Approved
0.6423	Remote Similarity	NPD6059	Approved
0.6389	Remote Similarity	NPD8034	Phase 2
0.6389	Remote Similarity	NPD8035	Phase 2
0.6378	Remote Similarity	NPD7078	Approved
0.6354	Remote Similarity	NPD2254	Approved
0.6354	Remote Similarity	NPD2686	Approved
0.6354	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4787	Phase 1
0.6354	Remote Similarity	NPD2687	Approved
0.6271	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.627	Remote Similarity	NPD8328	Phase 3
0.624	Remote Similarity	NPD6016	Approved
0.624	Remote Similarity	NPD6015	Approved
0.6214	Remote Similarity	NPD1780	Approved
0.6214	Remote Similarity	NPD1779	Approved
0.6207	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7638	Approved
0.619	Remote Similarity	NPD5988	Approved
0.6186	Remote Similarity	NPD6686	Approved
0.6186	Remote Similarity	NPD8174	Phase 2
0.6179	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD6008	Approved
0.6142	Remote Similarity	NPD6067	Discontinued
0.614	Remote Similarity	NPD7640	Approved
0.614	Remote Similarity	NPD7639	Approved
0.6132	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5777	Approved
0.6116	Remote Similarity	NPD6882	Approved
0.6116	Remote Similarity	NPD8297	Approved
0.61	Remote Similarity	NPD3703	Phase 2
0.6066	Remote Similarity	NPD4632	Approved
0.6064	Remote Similarity	NPD371	Approved
0.605	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7320	Approved
0.6034	Remote Similarity	NPD7632	Discontinued
0.6032	Remote Similarity	NPD6319	Approved
0.6028	Remote Similarity	NPD7625	Phase 1
0.602	Remote Similarity	NPD4244	Approved
0.602	Remote Similarity	NPD4245	Approved
0.6017	Remote Similarity	NPD5739	Approved
0.6017	Remote Similarity	NPD6675	Approved
0.6017	Remote Similarity	NPD7128	Approved
0.6017	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6015	Remote Similarity	NPD8449	Approved
0.597	Remote Similarity	NPD8450	Suspended
0.5962	Remote Similarity	NPD7525	Registered
0.5954	Remote Similarity	NPD6033	Approved
0.595	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7115	Discovery
0.5918	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD3698	Phase 2
0.5917	Remote Similarity	NPD6899	Approved
0.5917	Remote Similarity	NPD6881	Approved
0.5902	Remote Similarity	NPD8130	Phase 1
0.5868	Remote Similarity	NPD6373	Approved
0.5868	Remote Similarity	NPD6372	Approved
0.5862	Remote Similarity	NPD8418	Phase 2
0.5833	Remote Similarity	NPD5701	Approved
0.5833	Remote Similarity	NPD5697	Approved
0.582	Remote Similarity	NPD6883	Approved
0.582	Remote Similarity	NPD7290	Approved
0.582	Remote Similarity	NPD7102	Approved
0.5816	Remote Similarity	NPD5360	Phase 3
0.5816	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6081	Approved
0.5789	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6847	Approved
0.5772	Remote Similarity	NPD6650	Approved
0.5772	Remote Similarity	NPD6649	Approved
0.5772	Remote Similarity	NPD6617	Approved
0.5772	Remote Similarity	NPD6869	Approved
0.5738	Remote Similarity	NPD6013	Approved
0.5738	Remote Similarity	NPD6014	Approved
0.5738	Remote Similarity	NPD6012	Approved
0.5736	Remote Similarity	NPD8515	Approved
0.5736	Remote Similarity	NPD5983	Phase 2
0.5736	Remote Similarity	NPD8516	Approved
0.5736	Remote Similarity	NPD8513	Phase 3
0.5736	Remote Similarity	NPD8517	Approved
0.5714	Remote Similarity	NPD7755	Approved
0.5714	Remote Similarity	NPD7754	Approved
0.5702	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4789	Approved
0.569	Remote Similarity	NPD6084	Phase 2
0.569	Remote Similarity	NPD6083	Phase 2
0.5682	Remote Similarity	NPD6336	Discontinued
0.5678	Remote Similarity	NPD5344	Discontinued
0.5678	Remote Similarity	NPD4159	Approved
0.5656	Remote Similarity	NPD6011	Approved
0.5645	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD4802	Phase 2
0.5619	Remote Similarity	NPD4238	Approved
0.5614	Remote Similarity	NPD6399	Phase 3
0.5612	Remote Similarity	NPD4224	Phase 2

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