NPASS Compound

Structure

NPC64742 OpenBabel07101719132D 29 31 0 0 1 0 0 0 0 0999 V2000 0.1263 2.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6708 -2.4726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9599 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4455 -0.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2431 1.6201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4938 2.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9279 0.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4193 -0.2421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7012 -1.3566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7012 0.3883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7571 -1.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7571 0.6038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 3.2402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1253 -1.6725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 0.4842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0597 4.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 -1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 -0.4842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6772 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8059 -1.8173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9950 4.4262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3749 4.8603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 -2.4209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9599 -0.9684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5455 -0.8001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6772 -0.9684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 5 6 1 0 0 0 0 5 8 2 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 15 23 2 0 0 0 0 15 28 1 0 0 0 0 16 20 1 6 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 18 29 1 0 0 0 0 19 3 1 1 0 0 0 19 27 1 0 0 0 0 20 4 1 1 0 0 0 20 29 1 0 0 0 0 21 22 1 1 0 0 0 22 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	409.112
LogP:	1.224
LogD:	0.222
LogS:	-3.204
# Rotatable Bonds:	5
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	5.742
Fsp3:	0.591
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:	-5.433
MDCK Permeability:	1.2908381904708222e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.34
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.656
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.505
Plasma Protein Binding (PPB):	35.24236297607422%
Volume Distribution (VD):	0.28
Pgp-substrate:	31.239858627319336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.212
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.192
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	2.13
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.174
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.271
Skin Sensitization:	0.123
Carcinogencity:	0.897
Eye Corrosion:	0.014
Eye Irritation:	0.038
Respiratory Toxicity:	0.829

Download Data

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

Natural Product: NPC64742

Natural Product ID:	NPC64742
*Common Name:**	Pseudolaric Acid A2
IUPAC Name:	n.a.
Synonyms:	pseudolaric acid A2
Standard InCHIKey:	AROWACRIPDBCHW-MWVIGJKDSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-14(17(24)25)6-5-8-20(4)16-7-9-21(18(26)29-20)12-10-19(3,27)11-13-22(16,21)28-15(2)23/h5-6,8,10,12,16,27H,7,9,11,13H2,1-4H3,(H,24,25)/b8-5+,14-6+/t16-,19+,20+,21-,22-/m0/s1
SMILES:	C/C(=CC=C[C@]1(C)[C@@H]2CC[C@]3(C=C[C@](C)(CC[C@]23OC(=O)C)O)C(=O)O1)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253388
PubChem CID:	44444976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	PMID[14527554]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17291040]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root and trunk bark	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377017]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[465759]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[465759]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[465759]

☑ 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 NPC64742 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	187
0.1-0.2	1004
0.2-0.3	4025
0.3-0.4	8725
0.4-0.5	14631
0.5-0.6	7840
0.6-0.7	5324
0.7-0.8	937
0.8-0.85	12
0.85-0.9	4
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC9812
0.9574	High Similarity	NPC206079
0.957	High Similarity	NPC244411
0.9479	High Similarity	NPC309190
0.9368	High Similarity	NPC116139
0.9368	High Similarity	NPC62670
0.9271	High Similarity	NPC66110
0.8866	High Similarity	NPC280963
0.8854	High Similarity	NPC47834
0.8229	Intermediate Similarity	NPC77337
0.8198	Intermediate Similarity	NPC470829
0.8198	Intermediate Similarity	NPC473228
0.8144	Intermediate Similarity	NPC472705
0.8144	Intermediate Similarity	NPC45579
0.8119	Intermediate Similarity	NPC469872
0.8119	Intermediate Similarity	NPC469864
0.8091	Intermediate Similarity	NPC13710
0.8039	Intermediate Similarity	NPC477950
0.8022	Intermediate Similarity	NPC469617
0.802	Intermediate Similarity	NPC141191
0.7938	Intermediate Similarity	NPC212598
0.7921	Intermediate Similarity	NPC169205
0.7921	Intermediate Similarity	NPC202705
0.79	Intermediate Similarity	NPC469873
0.7895	Intermediate Similarity	NPC471185
0.7885	Intermediate Similarity	NPC183570
0.7885	Intermediate Similarity	NPC280566
0.7864	Intermediate Similarity	NPC475099
0.785	Intermediate Similarity	NPC47951
0.7849	Intermediate Similarity	NPC59994
0.7849	Intermediate Similarity	NPC78677
0.783	Intermediate Similarity	NPC476958
0.7822	Intermediate Similarity	NPC185553
0.7812	Intermediate Similarity	NPC234038
0.781	Intermediate Similarity	NPC272632
0.78	Intermediate Similarity	NPC167219
0.7798	Intermediate Similarity	NPC76550
0.7798	Intermediate Similarity	NPC138757
0.7798	Intermediate Similarity	NPC123855
0.7789	Intermediate Similarity	NPC14575
0.7789	Intermediate Similarity	NPC196487
0.7778	Intermediate Similarity	NPC261607
0.7778	Intermediate Similarity	NPC300312
0.7778	Intermediate Similarity	NPC111114
0.7767	Intermediate Similarity	NPC290802
0.7757	Intermediate Similarity	NPC220155
0.7755	Intermediate Similarity	NPC115179
0.7755	Intermediate Similarity	NPC212664
0.7755	Intermediate Similarity	NPC106040
0.7745	Intermediate Similarity	NPC108475
0.7745	Intermediate Similarity	NPC170143
0.7745	Intermediate Similarity	NPC477949
0.7745	Intermediate Similarity	NPC213947
0.7742	Intermediate Similarity	NPC47747
0.7727	Intermediate Similarity	NPC46269
0.7727	Intermediate Similarity	NPC106395
0.7723	Intermediate Similarity	NPC48803
0.7723	Intermediate Similarity	NPC171395
0.7723	Intermediate Similarity	NPC67584
0.7723	Intermediate Similarity	NPC90121
0.7723	Intermediate Similarity	NPC275960
0.7723	Intermediate Similarity	NPC209355
0.7723	Intermediate Similarity	NPC193645
0.7717	Intermediate Similarity	NPC222210
0.7717	Intermediate Similarity	NPC63445
0.7708	Intermediate Similarity	NPC245434
0.7708	Intermediate Similarity	NPC476628
0.77	Intermediate Similarity	NPC476049
0.7692	Intermediate Similarity	NPC469657
0.7692	Intermediate Similarity	NPC146822
0.7692	Intermediate Similarity	NPC244456
0.7692	Intermediate Similarity	NPC171759
0.7679	Intermediate Similarity	NPC476959
0.767	Intermediate Similarity	NPC222011
0.7658	Intermediate Similarity	NPC133677
0.7658	Intermediate Similarity	NPC138303
0.7658	Intermediate Similarity	NPC67290
0.7647	Intermediate Similarity	NPC213078
0.7642	Intermediate Similarity	NPC100487
0.7629	Intermediate Similarity	NPC198314
0.7629	Intermediate Similarity	NPC116575
0.7624	Intermediate Similarity	NPC53685
0.7619	Intermediate Similarity	NPC118405
0.76	Intermediate Similarity	NPC284185
0.76	Intermediate Similarity	NPC70595
0.76	Intermediate Similarity	NPC74103
0.76	Intermediate Similarity	NPC123177
0.76	Intermediate Similarity	NPC150978
0.76	Intermediate Similarity	NPC221282
0.7596	Intermediate Similarity	NPC227865
0.7573	Intermediate Similarity	NPC69385
0.7573	Intermediate Similarity	NPC161493
0.757	Intermediate Similarity	NPC314244
0.7549	Intermediate Similarity	NPC37408
0.7549	Intermediate Similarity	NPC52044
0.7549	Intermediate Similarity	NPC272050
0.7547	Intermediate Similarity	NPC329345
0.7547	Intermediate Similarity	NPC72151
0.7547	Intermediate Similarity	NPC473283
0.7547	Intermediate Similarity	NPC475526
0.7545	Intermediate Similarity	NPC474315
0.7527	Intermediate Similarity	NPC476627
0.7526	Intermediate Similarity	NPC474369
0.7524	Intermediate Similarity	NPC150923
0.75	Intermediate Similarity	NPC129419
0.75	Intermediate Similarity	NPC472866
0.75	Intermediate Similarity	NPC253144
0.75	Intermediate Similarity	NPC91034
0.75	Intermediate Similarity	NPC221615
0.75	Intermediate Similarity	NPC145666
0.75	Intermediate Similarity	NPC316598
0.7478	Intermediate Similarity	NPC476962
0.7477	Intermediate Similarity	NPC239162
0.7477	Intermediate Similarity	NPC121099
0.7477	Intermediate Similarity	NPC191620
0.7477	Intermediate Similarity	NPC203659
0.7477	Intermediate Similarity	NPC475970
0.7475	Intermediate Similarity	NPC58532
0.7475	Intermediate Similarity	NPC472677
0.7474	Intermediate Similarity	NPC325031
0.7455	Intermediate Similarity	NPC257240
0.7455	Intermediate Similarity	NPC477103
0.7455	Intermediate Similarity	NPC238850
0.7453	Intermediate Similarity	NPC475320
0.7453	Intermediate Similarity	NPC475091
0.7453	Intermediate Similarity	NPC478156
0.7453	Intermediate Similarity	NPC320447
0.7451	Intermediate Similarity	NPC90453
0.7451	Intermediate Similarity	NPC96541
0.7451	Intermediate Similarity	NPC65829
0.7451	Intermediate Similarity	NPC127019
0.7451	Intermediate Similarity	NPC477131
0.7449	Intermediate Similarity	NPC6247
0.7447	Intermediate Similarity	NPC472013
0.7447	Intermediate Similarity	NPC84185
0.7447	Intermediate Similarity	NPC66677
0.7447	Intermediate Similarity	NPC471890
0.7447	Intermediate Similarity	NPC476624
0.7431	Intermediate Similarity	NPC473482
0.7431	Intermediate Similarity	NPC475418
0.7431	Intermediate Similarity	NPC318363
0.7429	Intermediate Similarity	NPC241221
0.7429	Intermediate Similarity	NPC475053
0.7429	Intermediate Similarity	NPC477521
0.7426	Intermediate Similarity	NPC473986
0.7426	Intermediate Similarity	NPC472814
0.7426	Intermediate Similarity	NPC177037
0.7426	Intermediate Similarity	NPC204341
0.7426	Intermediate Similarity	NPC474018
0.7423	Intermediate Similarity	NPC156485
0.7414	Intermediate Similarity	NPC46570
0.7407	Intermediate Similarity	NPC243998
0.7407	Intermediate Similarity	NPC223450
0.7404	Intermediate Similarity	NPC40812
0.74	Intermediate Similarity	NPC12872
0.74	Intermediate Similarity	NPC268298
0.74	Intermediate Similarity	NPC168679
0.7387	Intermediate Similarity	NPC179798
0.7387	Intermediate Similarity	NPC304180
0.7383	Intermediate Similarity	NPC475871
0.7383	Intermediate Similarity	NPC110989
0.7383	Intermediate Similarity	NPC475945
0.7383	Intermediate Similarity	NPC470954
0.7383	Intermediate Similarity	NPC472755
0.7379	Intermediate Similarity	NPC304886
0.7379	Intermediate Similarity	NPC170120
0.7379	Intermediate Similarity	NPC293052
0.7379	Intermediate Similarity	NPC213698
0.7374	Intermediate Similarity	NPC113370
0.7374	Intermediate Similarity	NPC191283
0.7374	Intermediate Similarity	NPC128644
0.7374	Intermediate Similarity	NPC476079
0.7374	Intermediate Similarity	NPC201658
0.7374	Intermediate Similarity	NPC86005
0.7374	Intermediate Similarity	NPC231599
0.7374	Intermediate Similarity	NPC478145
0.7374	Intermediate Similarity	NPC103743
0.7368	Intermediate Similarity	NPC164218
0.7368	Intermediate Similarity	NPC239273
0.7368	Intermediate Similarity	NPC471145
0.7364	Intermediate Similarity	NPC228477
0.7364	Intermediate Similarity	NPC137911
0.7364	Intermediate Similarity	NPC477102
0.7364	Intermediate Similarity	NPC475065
0.7358	Intermediate Similarity	NPC476240
0.7358	Intermediate Similarity	NPC474742
0.7358	Intermediate Similarity	NPC282524
0.7358	Intermediate Similarity	NPC224720
0.7358	Intermediate Similarity	NPC476223
0.7358	Intermediate Similarity	NPC469851
0.7358	Intermediate Similarity	NPC472753
0.7358	Intermediate Similarity	NPC99411
0.7353	Intermediate Similarity	NPC473234
0.7353	Intermediate Similarity	NPC40821
0.7353	Intermediate Similarity	NPC115021
0.7353	Intermediate Similarity	NPC32862
0.7353	Intermediate Similarity	NPC473263
0.7353	Intermediate Similarity	NPC308656
0.7353	Intermediate Similarity	NPC472871
0.7353	Intermediate Similarity	NPC272293

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 NPC64742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1244
0.2-0.3	3507
0.3-0.4	2773
0.4-0.5	934
0.5-0.6	285
0.6-0.7	222
0.7-0.8	20
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
0.7723	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5785	Approved
0.7455	Intermediate Similarity	NPD6371	Approved
0.7255	Intermediate Similarity	NPD5281	Approved
0.7255	Intermediate Similarity	NPD6411	Approved
0.7255	Intermediate Similarity	NPD5284	Approved
0.7184	Intermediate Similarity	NPD5779	Approved
0.7184	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5363	Approved
0.71	Intermediate Similarity	NPD5786	Approved
0.7087	Intermediate Similarity	NPD7637	Suspended
0.7069	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6101	Approved
0.7041	Intermediate Similarity	NPD5209	Approved
0.7027	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5697	Approved
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.697	Remote Similarity	NPD5362	Discontinued
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD5694	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD7983	Approved
0.6903	Remote Similarity	NPD6012	Approved
0.6903	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD6014	Approved
0.6887	Remote Similarity	NPD5695	Phase 3
0.6869	Remote Similarity	NPD6435	Approved
0.6869	Remote Similarity	NPD4270	Approved
0.6869	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4269	Approved
0.6852	Remote Similarity	NPD4225	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6837	Remote Similarity	NPD4819	Approved
0.6837	Remote Similarity	NPD4821	Approved
0.6837	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4822	Approved
0.6837	Remote Similarity	NPD4820	Approved
0.6827	Remote Similarity	NPD5692	Phase 3
0.6827	Remote Similarity	NPD5207	Approved
0.6822	Remote Similarity	NPD7839	Suspended
0.6818	Remote Similarity	NPD5211	Phase 2
0.6814	Remote Similarity	NPD6011	Approved
0.6804	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4518	Approved
0.6792	Remote Similarity	NPD5282	Discontinued
0.6786	Remote Similarity	NPD5739	Approved
0.6786	Remote Similarity	NPD6675	Approved
0.6786	Remote Similarity	NPD7128	Approved
0.6786	Remote Similarity	NPD6402	Approved
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6650	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6649	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6768	Remote Similarity	NPD5369	Approved
0.6762	Remote Similarity	NPD6050	Approved
0.6759	Remote Similarity	NPD6084	Phase 2
0.6759	Remote Similarity	NPD6083	Phase 2
0.6726	Remote Similarity	NPD5701	Approved
0.6724	Remote Similarity	NPD8297	Approved
0.6724	Remote Similarity	NPD6882	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6634	Remote Similarity	NPD7154	Phase 3
0.6633	Remote Similarity	NPD4271	Approved
0.6633	Remote Similarity	NPD4268	Approved
0.6612	Remote Similarity	NPD6319	Approved
0.6609	Remote Similarity	NPD6372	Approved
0.6609	Remote Similarity	NPD6373	Approved
0.6602	Remote Similarity	NPD4694	Approved
0.6602	Remote Similarity	NPD5280	Approved
0.6602	Remote Similarity	NPD5690	Phase 2
0.6602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7319	Approved
0.6571	Remote Similarity	NPD6904	Approved
0.6571	Remote Similarity	NPD6673	Approved
0.6571	Remote Similarity	NPD1695	Approved
0.6571	Remote Similarity	NPD6080	Approved
0.6545	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6399	Phase 3
0.6538	Remote Similarity	NPD3573	Approved
0.6535	Remote Similarity	NPD4221	Approved
0.6535	Remote Similarity	NPD4223	Phase 3
0.6522	Remote Similarity	NPD6686	Approved
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6509	Remote Similarity	NPD7838	Discovery
0.6505	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD1694	Approved
0.6495	Remote Similarity	NPD8039	Approved
0.6486	Remote Similarity	NPD6404	Discontinued
0.6486	Remote Similarity	NPD7640	Approved
0.6486	Remote Similarity	NPD7639	Approved
0.648	Remote Similarity	NPD7507	Approved
0.6476	Remote Similarity	NPD5208	Approved
0.6471	Remote Similarity	NPD5332	Approved
0.6471	Remote Similarity	NPD5331	Approved
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD4755	Approved
0.6442	Remote Similarity	NPD4249	Approved
0.6436	Remote Similarity	NPD4790	Discontinued
0.6429	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD8517	Approved
0.6423	Remote Similarity	NPD8516	Approved
0.6423	Remote Similarity	NPD8515	Approved
0.6423	Remote Similarity	NPD8513	Phase 3
0.6422	Remote Similarity	NPD5654	Approved
0.6422	Remote Similarity	NPD5210	Approved
0.6422	Remote Similarity	NPD4629	Approved
0.6417	Remote Similarity	NPD6274	Approved
0.6415	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD4634	Approved
0.6408	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4197	Approved
0.64	Remote Similarity	NPD7492	Approved
0.6396	Remote Similarity	NPD7638	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6387	Remote Similarity	NPD4632	Approved
0.6381	Remote Similarity	NPD4251	Approved
0.6381	Remote Similarity	NPD4250	Approved
0.6364	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD6317	Approved
0.6357	Remote Similarity	NPD7260	Phase 2
0.6356	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4096	Approved
0.6349	Remote Similarity	NPD6616	Approved
0.6348	Remote Similarity	NPD6008	Approved
0.6346	Remote Similarity	NPD5329	Approved
0.6341	Remote Similarity	NPD6054	Approved
0.6339	Remote Similarity	NPD4700	Approved
0.6339	Remote Similarity	NPD6648	Approved
0.6321	Remote Similarity	NPD6672	Approved
0.6321	Remote Similarity	NPD5737	Approved
0.6311	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD6695	Phase 3
0.6311	Remote Similarity	NPD6313	Approved
0.6311	Remote Similarity	NPD6314	Approved
0.6306	Remote Similarity	NPD5959	Approved
0.6299	Remote Similarity	NPD7078	Approved
0.6296	Remote Similarity	NPD6079	Approved
0.629	Remote Similarity	NPD7503	Approved
0.629	Remote Similarity	NPD6016	Approved
0.629	Remote Similarity	NPD6015	Approved
0.6286	Remote Similarity	NPD4693	Phase 3
0.6286	Remote Similarity	NPD7334	Approved
0.6286	Remote Similarity	NPD6684	Approved
0.6286	Remote Similarity	NPD5205	Approved
0.6286	Remote Similarity	NPD5330	Approved
0.6286	Remote Similarity	NPD7146	Approved
0.6286	Remote Similarity	NPD7521	Approved
0.6286	Remote Similarity	NPD6098	Approved
0.6286	Remote Similarity	NPD4688	Approved
0.6286	Remote Similarity	NPD4690	Approved
0.6286	Remote Similarity	NPD4689	Approved
0.6286	Remote Similarity	NPD6409	Approved
0.6286	Remote Similarity	NPD4138	Approved
0.6286	Remote Similarity	NPD4623	Approved
0.6286	Remote Similarity	NPD4519	Discontinued
0.6286	Remote Similarity	NPD5279	Phase 3
0.6273	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7736	Approved
0.624	Remote Similarity	NPD5988	Approved
0.624	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6238	Remote Similarity	NPD4195	Approved
0.623	Remote Similarity	NPD6009	Approved
0.6216	Remote Similarity	NPD5221	Approved
0.6216	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5222	Approved
0.6214	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6001	Approved
0.6176	Remote Similarity	NPD4695	Discontinued
0.6172	Remote Similarity	NPD8074	Phase 3
0.617	Remote Similarity	NPD7331	Phase 2
0.6168	Remote Similarity	NPD6903	Approved
0.6168	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5173	Approved
0.616	Remote Similarity	NPD5983	Phase 2
0.616	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5344	Discontinued
0.6134	Remote Similarity	NPD5247	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