NPASS Compound

Structure

CID65661 OpenBabel06191715402D 24 26 0 0 1 0 0 0 0 0999 V2000 2.8147 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4128 1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2788 1.2024 0.0000 C 0 0 2 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 7.7788 2.0685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 2.9345 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 13 2 0 0 0 0 4 10 1 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 19 1 1 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	3.849
LogD:	3.628
LogS:	-3.854
# Rotatable Bonds:	4
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	4.253
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.666
MDCK Permeability:	1.3842251973983366e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	92.16697692871094%
Volume Distribution (VD):	0.679
Pgp-substrate:	4.959287643432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.271
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.228
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	2.206
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.694
Maximum Recommended Daily Dose:	0.745
Skin Sensitization:	0.206
Carcinogencity:	0.525
Eye Corrosion:	0.061
Eye Irritation:	0.347
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC65661

Natural Product ID:	NPC65661
*Common Name:**	Pinusolidic Acid
IUPAC Name:	(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:	Pinusolidic Acid
Standard InCHIKey:	FHQSDRHZGCMBKG-FIYPYCPBSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-13-5-8-16-19(2,10-4-11-20(16,3)18(22)23)15(13)7-6-14-9-12-24-17(14)21/h9,15-16H,1,4-8,10-12H2,2-3H3,(H,22,23)/p-1/t15-,16+,19+,20-/m0/s1
SMILES:	C=C1CC[C@@H]2[C@](C)(CCC[C@]2(C)C(=O)[O-])[C@H]1CCC1=CCOC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465159
PubChem CID:	25880646
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
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28256	Platycladus orientalis	Species	Cupressaceae	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
EC50	1
IC50	6
Others	4

Activity Type	# Activity
Cell Line	6
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	750000.0	nM	PMID[537282]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[537284]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[537284]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[537284]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[537284]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[537284]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	EC50	=	4710.0	nM	PMID[537282]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	159.0	n.a.	PMID[537282]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	Inhibition	<	25.0	%	PMID[537282]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	163900.0	nM	PMID[537283]

☑ 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 NPC65661 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	174
0.1-0.2	979
0.2-0.3	4147
0.3-0.4	10646
0.4-0.5	11973
0.5-0.6	6819
0.6-0.7	5804
0.7-0.8	1926
0.8-0.85	169
0.85-0.9	43
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC86316
0.975	High Similarity	NPC106416
0.962	High Similarity	NPC200513
0.9518	High Similarity	NPC174342
0.9405	High Similarity	NPC51486
0.9294	High Similarity	NPC477783
0.9286	High Similarity	NPC5509
0.925	High Similarity	NPC14203
0.925	High Similarity	NPC229584
0.925	High Similarity	NPC40228
0.9186	High Similarity	NPC139692
0.9176	High Similarity	NPC477782
0.907	High Similarity	NPC472814
0.907	High Similarity	NPC177037
0.9059	High Similarity	NPC251528
0.9036	High Similarity	NPC30984
0.9036	High Similarity	NPC189311
0.8977	High Similarity	NPC209355
0.8876	High Similarity	NPC234993
0.8876	High Similarity	NPC242848
0.8876	High Similarity	NPC134072
0.8875	High Similarity	NPC198240
0.8837	High Similarity	NPC168131
0.8778	High Similarity	NPC475709
0.8764	High Similarity	NPC293052
0.875	High Similarity	NPC115021
0.875	High Similarity	NPC472303
0.875	High Similarity	NPC61952
0.8721	High Similarity	NPC226863
0.869	High Similarity	NPC149869
0.8667	High Similarity	NPC29952
0.8652	High Similarity	NPC476415
0.8642	High Similarity	NPC59436
0.8636	High Similarity	NPC289479
0.8636	High Similarity	NPC470113
0.8605	High Similarity	NPC312561
0.8587	High Similarity	NPC471413
0.8571	High Similarity	NPC474343
0.8571	High Similarity	NPC311070
0.8571	High Similarity	NPC22611
0.8556	High Similarity	NPC295347
0.8554	High Similarity	NPC90055
0.8539	High Similarity	NPC472871
0.8523	High Similarity	NPC476369
0.8523	High Similarity	NPC232426
0.8523	High Similarity	NPC281942
0.8523	High Similarity	NPC476437
0.8519	High Similarity	NPC316500
0.8506	High Similarity	NPC472302
0.8506	High Similarity	NPC472870
0.8495	Intermediate Similarity	NPC471412
0.8488	Intermediate Similarity	NPC131813
0.8478	Intermediate Similarity	NPC98868
0.8471	Intermediate Similarity	NPC248758
0.8471	Intermediate Similarity	NPC19849
0.8471	Intermediate Similarity	NPC472864
0.8471	Intermediate Similarity	NPC475100
0.8427	Intermediate Similarity	NPC72845
0.8427	Intermediate Similarity	NPC141831
0.8427	Intermediate Similarity	NPC303697
0.8415	Intermediate Similarity	NPC239098
0.8409	Intermediate Similarity	NPC474396
0.8409	Intermediate Similarity	NPC66344
0.8409	Intermediate Similarity	NPC50488
0.8404	Intermediate Similarity	NPC162973
0.8387	Intermediate Similarity	NPC117685
0.8387	Intermediate Similarity	NPC201406
0.8387	Intermediate Similarity	NPC474012
0.8387	Intermediate Similarity	NPC476767
0.8387	Intermediate Similarity	NPC476299
0.8387	Intermediate Similarity	NPC477720
0.837	Intermediate Similarity	NPC208094
0.837	Intermediate Similarity	NPC253826
0.8353	Intermediate Similarity	NPC97913
0.8353	Intermediate Similarity	NPC193198
0.8352	Intermediate Similarity	NPC183012
0.8333	Intermediate Similarity	NPC152778
0.8333	Intermediate Similarity	NPC162615
0.8333	Intermediate Similarity	NPC151722
0.8333	Intermediate Similarity	NPC475657
0.8333	Intermediate Similarity	NPC205034
0.8333	Intermediate Similarity	NPC476416
0.8333	Intermediate Similarity	NPC166346
0.8316	Intermediate Similarity	NPC180204
0.8316	Intermediate Similarity	NPC112009
0.8315	Intermediate Similarity	NPC8062
0.8315	Intermediate Similarity	NPC159748
0.8315	Intermediate Similarity	NPC310479
0.8315	Intermediate Similarity	NPC101651
0.8315	Intermediate Similarity	NPC472866
0.8315	Intermediate Similarity	NPC182136
0.8313	Intermediate Similarity	NPC327674
0.8298	Intermediate Similarity	NPC303559
0.8298	Intermediate Similarity	NPC63249
0.8295	Intermediate Similarity	NPC104560
0.8295	Intermediate Similarity	NPC472810
0.8295	Intermediate Similarity	NPC472809
0.828	Intermediate Similarity	NPC108368
0.828	Intermediate Similarity	NPC316598
0.828	Intermediate Similarity	NPC57079
0.8276	Intermediate Similarity	NPC474062
0.8276	Intermediate Similarity	NPC472869
0.8276	Intermediate Similarity	NPC186975
0.8261	Intermediate Similarity	NPC319692
0.8261	Intermediate Similarity	NPC325960
0.8261	Intermediate Similarity	NPC470801
0.8256	Intermediate Similarity	NPC71626
0.8256	Intermediate Similarity	NPC164577
0.8256	Intermediate Similarity	NPC472865
0.8256	Intermediate Similarity	NPC30486
0.8242	Intermediate Similarity	NPC84893
0.8242	Intermediate Similarity	NPC57117
0.8235	Intermediate Similarity	NPC186276
0.8235	Intermediate Similarity	NPC94200
0.8228	Intermediate Similarity	NPC67183
0.8222	Intermediate Similarity	NPC165904
0.8222	Intermediate Similarity	NPC474018
0.8222	Intermediate Similarity	NPC476187
0.8222	Intermediate Similarity	NPC65513
0.8222	Intermediate Similarity	NPC179517
0.8222	Intermediate Similarity	NPC473986
0.8214	Intermediate Similarity	NPC195424
0.8211	Intermediate Similarity	NPC134077
0.8211	Intermediate Similarity	NPC476769
0.8211	Intermediate Similarity	NPC476081
0.8193	Intermediate Similarity	NPC471220
0.8191	Intermediate Similarity	NPC54705
0.8182	Intermediate Similarity	NPC236618
0.8172	Intermediate Similarity	NPC476253
0.8161	Intermediate Similarity	NPC42586
0.8161	Intermediate Similarity	NPC473251
0.8152	Intermediate Similarity	NPC33473
0.8148	Intermediate Similarity	NPC20025
0.814	Intermediate Similarity	NPC215893
0.814	Intermediate Similarity	NPC477124
0.8132	Intermediate Similarity	NPC169343
0.8125	Intermediate Similarity	NPC120321
0.8118	Intermediate Similarity	NPC325031
0.8118	Intermediate Similarity	NPC327002
0.8118	Intermediate Similarity	NPC282293
0.8118	Intermediate Similarity	NPC278459
0.8111	Intermediate Similarity	NPC221111
0.8111	Intermediate Similarity	NPC469595
0.8111	Intermediate Similarity	NPC280149
0.8111	Intermediate Similarity	NPC220454
0.8111	Intermediate Similarity	NPC212679
0.8111	Intermediate Similarity	NPC198818
0.8111	Intermediate Similarity	NPC78973
0.8111	Intermediate Similarity	NPC471818
0.8105	Intermediate Similarity	NPC472643
0.8105	Intermediate Similarity	NPC475099
0.8095	Intermediate Similarity	NPC263951
0.8095	Intermediate Similarity	NPC150646
0.809	Intermediate Similarity	NPC117122
0.809	Intermediate Similarity	NPC24816
0.8085	Intermediate Similarity	NPC23364
0.8072	Intermediate Similarity	NPC97377
0.8072	Intermediate Similarity	NPC165711
0.8072	Intermediate Similarity	NPC189206
0.8068	Intermediate Similarity	NPC471219
0.8068	Intermediate Similarity	NPC185638
0.8068	Intermediate Similarity	NPC220478
0.8068	Intermediate Similarity	NPC329692
0.8065	Intermediate Similarity	NPC473153
0.8065	Intermediate Similarity	NPC16967
0.8065	Intermediate Similarity	NPC202833
0.8049	Intermediate Similarity	NPC476795
0.8046	Intermediate Similarity	NPC318515
0.8043	Intermediate Similarity	NPC53685
0.8043	Intermediate Similarity	NPC191521
0.8043	Intermediate Similarity	NPC474554
0.8043	Intermediate Similarity	NPC471040
0.8043	Intermediate Similarity	NPC477130
0.8043	Intermediate Similarity	NPC477129
0.8023	Intermediate Similarity	NPC471159
0.8023	Intermediate Similarity	NPC178676
0.8023	Intermediate Similarity	NPC142683
0.8023	Intermediate Similarity	NPC123880
0.8022	Intermediate Similarity	NPC186363
0.8022	Intermediate Similarity	NPC472811
0.8022	Intermediate Similarity	NPC329842
0.8022	Intermediate Similarity	NPC233345
0.8021	Intermediate Similarity	NPC114540
0.8021	Intermediate Similarity	NPC40918
0.8021	Intermediate Similarity	NPC155332
0.8021	Intermediate Similarity	NPC32577
0.8	Intermediate Similarity	NPC284561
0.8	Intermediate Similarity	NPC10636
0.8	Intermediate Similarity	NPC476303
0.8	Intermediate Similarity	NPC472644
0.8	Intermediate Similarity	NPC104545
0.8	Intermediate Similarity	NPC470734
0.8	Intermediate Similarity	NPC47024
0.8	Intermediate Similarity	NPC471041
0.798	Intermediate Similarity	NPC177524
0.798	Intermediate Similarity	NPC219900
0.798	Intermediate Similarity	NPC392
0.7979	Intermediate Similarity	NPC38530
0.7979	Intermediate Similarity	NPC476768
0.7979	Intermediate Similarity	NPC202705

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 NPC65661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1270
0.2-0.3	3570
0.3-0.4	2675
0.4-0.5	955
0.5-0.6	276
0.6-0.7	201
0.7-0.8	55
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.962	High Similarity	NPD4752	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD6686	Approved
0.7895	Intermediate Similarity	NPD7638	Approved
0.7895	Intermediate Similarity	NPD4225	Approved
0.7812	Intermediate Similarity	NPD7640	Approved
0.7812	Intermediate Similarity	NPD7639	Approved
0.7753	Intermediate Similarity	NPD1694	Approved
0.7692	Intermediate Similarity	NPD6672	Approved
0.7692	Intermediate Similarity	NPD5737	Approved
0.7667	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD7146	Approved
0.7667	Intermediate Similarity	NPD6409	Approved
0.7667	Intermediate Similarity	NPD6684	Approved
0.7667	Intermediate Similarity	NPD5330	Approved
0.7667	Intermediate Similarity	NPD7521	Approved
0.766	Intermediate Similarity	NPD7748	Approved
0.7634	Intermediate Similarity	NPD5693	Phase 1
0.7604	Intermediate Similarity	NPD6083	Phase 2
0.7604	Intermediate Similarity	NPD6084	Phase 2
0.7586	Intermediate Similarity	NPD4695	Discontinued
0.7579	Intermediate Similarity	NPD5695	Phase 3
0.7553	Intermediate Similarity	NPD6399	Phase 3
0.7526	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7515	Phase 2
0.7444	Intermediate Similarity	NPD3665	Phase 1
0.7444	Intermediate Similarity	NPD3666	Approved
0.7444	Intermediate Similarity	NPD3133	Approved
0.7423	Intermediate Similarity	NPD7902	Approved
0.7412	Intermediate Similarity	NPD8039	Approved
0.734	Intermediate Similarity	NPD5785	Approved
0.7283	Intermediate Similarity	NPD3618	Phase 1
0.7283	Intermediate Similarity	NPD4623	Approved
0.7283	Intermediate Similarity	NPD4519	Discontinued
0.7234	Intermediate Similarity	NPD6673	Approved
0.7234	Intermediate Similarity	NPD6080	Approved
0.7234	Intermediate Similarity	NPD4753	Phase 2
0.7234	Intermediate Similarity	NPD6904	Approved
0.7222	Intermediate Similarity	NPD4223	Phase 3
0.7222	Intermediate Similarity	NPD7115	Discovery
0.7222	Intermediate Similarity	NPD4221	Approved
0.7222	Intermediate Similarity	NPD3667	Approved
0.7216	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3573	Approved
0.7184	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7632	Discontinued
0.7128	Intermediate Similarity	NPD5208	Approved
0.7115	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD6881	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7113	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7900	Approved
0.7097	Intermediate Similarity	NPD5279	Phase 3
0.7097	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7083	Intermediate Similarity	NPD6079	Approved
0.7083	Intermediate Similarity	NPD5284	Approved
0.7083	Intermediate Similarity	NPD5281	Approved
0.7065	Intermediate Similarity	NPD4786	Approved
0.7065	Intermediate Similarity	NPD4197	Approved
0.7065	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5328	Approved
0.7053	Intermediate Similarity	NPD6051	Approved
0.7053	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.7048	Intermediate Similarity	NPD6013	Approved
0.7041	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4629	Approved
0.7041	Intermediate Similarity	NPD5210	Approved
0.7033	Intermediate Similarity	NPD5209	Approved
0.7019	Intermediate Similarity	NPD5701	Approved
0.6989	Remote Similarity	NPD5329	Approved
0.6981	Remote Similarity	NPD6883	Approved
0.6981	Remote Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD7102	Approved
0.6979	Remote Similarity	NPD46	Approved
0.6979	Remote Similarity	NPD5692	Phase 3
0.6979	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5221	Approved
0.697	Remote Similarity	NPD5222	Approved
0.6966	Remote Similarity	NPD3617	Approved
0.6966	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7320	Approved
0.6931	Remote Similarity	NPD6404	Discontinued
0.6916	Remote Similarity	NPD6650	Approved
0.6916	Remote Similarity	NPD6869	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6916	Remote Similarity	NPD6617	Approved
0.6916	Remote Similarity	NPD6649	Approved
0.6916	Remote Similarity	NPD6847	Approved
0.6915	Remote Similarity	NPD4690	Approved
0.6915	Remote Similarity	NPD4689	Approved
0.6915	Remote Similarity	NPD4693	Phase 3
0.6915	Remote Similarity	NPD4138	Approved
0.6915	Remote Similarity	NPD5205	Approved
0.6915	Remote Similarity	NPD6098	Approved
0.6915	Remote Similarity	NPD4688	Approved
0.6915	Remote Similarity	NPD5690	Phase 2
0.6907	Remote Similarity	NPD6050	Approved
0.6907	Remote Similarity	NPD7637	Suspended
0.6907	Remote Similarity	NPD8034	Phase 2
0.6907	Remote Similarity	NPD8035	Phase 2
0.6907	Remote Similarity	NPD5694	Approved
0.6907	Remote Similarity	NPD6411	Approved
0.69	Remote Similarity	NPD5173	Approved
0.6887	Remote Similarity	NPD6372	Approved
0.6887	Remote Similarity	NPD6373	Approved
0.6882	Remote Similarity	NPD3668	Phase 3
0.6857	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6837	Remote Similarity	NPD5779	Approved
0.6837	Remote Similarity	NPD4202	Approved
0.6837	Remote Similarity	NPD5778	Approved
0.6809	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5207	Approved
0.68	Remote Similarity	NPD7614	Phase 1
0.68	Remote Similarity	NPD4697	Phase 3
0.6796	Remote Similarity	NPD5211	Phase 2
0.6774	Remote Similarity	NPD7154	Phase 3
0.6774	Remote Similarity	NPD5362	Discontinued
0.6774	Remote Similarity	NPD4788	Approved
0.6768	Remote Similarity	NPD6001	Approved
0.6765	Remote Similarity	NPD5285	Approved
0.6765	Remote Similarity	NPD5286	Approved
0.6765	Remote Similarity	NPD4696	Approved
0.6759	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4691	Approved
0.6737	Remote Similarity	NPD4694	Approved
0.6737	Remote Similarity	NPD5280	Approved
0.6733	Remote Similarity	NPD4755	Approved
0.6724	Remote Similarity	NPD7507	Approved
0.6703	Remote Similarity	NPD4195	Approved
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6699	Remote Similarity	NPD5223	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD4632	Approved
0.6635	Remote Similarity	NPD4633	Approved
0.6635	Remote Similarity	NPD5224	Approved
0.6635	Remote Similarity	NPD5226	Approved
0.6635	Remote Similarity	NPD5225	Approved
0.6634	Remote Similarity	NPD7732	Phase 3
0.6632	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4137	Phase 3
0.6607	Remote Similarity	NPD6317	Approved
0.6604	Remote Similarity	NPD6008	Approved
0.6602	Remote Similarity	NPD4700	Approved
0.6571	Remote Similarity	NPD5174	Approved
0.6571	Remote Similarity	NPD5175	Approved
0.6555	Remote Similarity	NPD7319	Approved
0.6552	Remote Similarity	NPD4747	Approved
0.6549	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD6313	Approved
0.6549	Remote Similarity	NPD6314	Approved
0.6548	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5654	Approved
0.6517	Remote Similarity	NPD4058	Approved
0.6491	Remote Similarity	NPD7101	Approved
0.6491	Remote Similarity	NPD7100	Approved
0.6489	Remote Similarity	NPD4270	Approved
0.6489	Remote Similarity	NPD4269	Approved
0.6489	Remote Similarity	NPD6435	Approved
0.6484	Remote Similarity	NPD4756	Discovery
0.6465	Remote Similarity	NPD7838	Discovery
0.6465	Remote Similarity	NPD4096	Approved
0.646	Remote Similarity	NPD6009	Approved
0.6452	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3702	Approved
0.6436	Remote Similarity	NPD5282	Discontinued
0.6435	Remote Similarity	NPD6319	Approved
0.6429	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6695	Phase 3
0.6415	Remote Similarity	NPD6052	Approved
0.6415	Remote Similarity	NPD4754	Approved
0.6408	Remote Similarity	NPD5959	Approved
0.6404	Remote Similarity	NPD7328	Approved
0.6404	Remote Similarity	NPD7327	Approved
0.6392	Remote Similarity	NPD5786	Approved
0.6389	Remote Similarity	NPD6614	Approved
0.6383	Remote Similarity	NPD5369	Approved
0.6381	Remote Similarity	NPD5344	Discontinued
0.6379	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5983	Phase 2
0.6374	Remote Similarity	NPD3701	Clinical (unspecified phase)

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