NPASS Compound

Structure

NPC476369 OpenBabel07101719152D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.8228 -3.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1498 -4.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2609 -0.8998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8569 -3.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3914 -1.8912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 6 26 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 1 0 0 0 17 23 2 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 21 1 1 0 0 0 20 21 1 1 0 0 0 21 5 1 6 0 0 0 22 14 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.25
Volume:	390.65
LogP:	3.479
LogD:	2.915
LogS:	-4.22
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	4.908
Fsp3:	0.818
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:	-5.254
MDCK Permeability:	5.0342172471573576e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	93.8256607055664%
Volume Distribution (VD):	0.403
Pgp-substrate:	5.937246799468994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.217
CYP2C9-substrate:	0.251
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.533

ADMET: Excretion

Clearance (CL):	2.094
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.735
Skin Sensitization:	0.862
Carcinogencity:	0.341
Eye Corrosion:	0.082
Eye Irritation:	0.744
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC476369

Natural Product ID:	NPC476369
*Common Name:**	13Beta-Methoxy-7-Oxo-8(14)-Abieten-18-Oic Acid
IUPAC Name:	(1R,4aR,4bR,7S,10aR)-7-methoxy-1,4a,10a-trimethyl-9-oxo-7-propan-2-yl-3,4,4b,5,6,10-hexahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	NEAXSZFUWQAJJD-GVJIXFOXSA-N
Standard InCHI:	InChI=1S/C22H34O4/c1-14(2)22(26-6)11-8-16-15(12-22)17(23)13-21(5)19(16,3)9-7-10-20(21,4)18(24)25/h12,14,16H,7-11,13H2,1-6H3,(H,24,25)/t16-,19+,20-,21+,22+/m0/s1
SMILES:	CO[C@@]1(CC[C@H]2C(=C1)C(=O)C[C@@]1([C@]2(C)CCC[C@@]1(C)C(=O)O)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL589894
PubChem CID:	46230360
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	61.6	ug.mL-1	PMID[469445]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[469445]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[469445]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[469445]

☑ 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 NPC476369 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	193
0.1-0.2	1115
0.2-0.3	4284
0.3-0.4	10239
0.4-0.5	12506
0.5-0.6	7228
0.6-0.7	5118
0.7-0.8	1881
0.8-0.85	109
0.85-0.9	18
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476437
0.9412	High Similarity	NPC476409
0.9213	High Similarity	NPC476415
0.8929	High Similarity	NPC40228
0.8889	High Similarity	NPC476416
0.8824	High Similarity	NPC302661
0.8824	High Similarity	NPC238991
0.8721	High Similarity	NPC102197
0.8706	High Similarity	NPC278459
0.8621	High Similarity	NPC476412
0.8571	High Similarity	NPC472975
0.8571	High Similarity	NPC230064
0.8556	High Similarity	NPC5509
0.8539	High Similarity	NPC477228
0.8523	High Similarity	NPC65661
0.8511	High Similarity	NPC253826
0.8488	Intermediate Similarity	NPC14203
0.8488	Intermediate Similarity	NPC229584
0.8478	Intermediate Similarity	NPC472871
0.8478	Intermediate Similarity	NPC131840
0.8462	Intermediate Similarity	NPC198818
0.8462	Intermediate Similarity	NPC51486
0.8452	Intermediate Similarity	NPC165711
0.8444	Intermediate Similarity	NPC48107
0.8444	Intermediate Similarity	NPC472870
0.8409	Intermediate Similarity	NPC149869
0.8353	Intermediate Similarity	NPC198240
0.8353	Intermediate Similarity	NPC321514
0.8352	Intermediate Similarity	NPC469546
0.8352	Intermediate Similarity	NPC174342
0.8352	Intermediate Similarity	NPC262043
0.8333	Intermediate Similarity	NPC136948
0.8316	Intermediate Similarity	NPC170131
0.8315	Intermediate Similarity	NPC189311
0.8315	Intermediate Similarity	NPC86316
0.8315	Intermediate Similarity	NPC474680
0.8315	Intermediate Similarity	NPC106416
0.8298	Intermediate Similarity	NPC171395
0.8295	Intermediate Similarity	NPC49019
0.828	Intermediate Similarity	NPC169343
0.8276	Intermediate Similarity	NPC90055
0.8276	Intermediate Similarity	NPC471898
0.8247	Intermediate Similarity	NPC323441
0.8242	Intermediate Similarity	NPC72397
0.8235	Intermediate Similarity	NPC61952
0.8235	Intermediate Similarity	NPC97377
0.8235	Intermediate Similarity	NPC472300
0.8222	Intermediate Similarity	NPC322159
0.8222	Intermediate Similarity	NPC220478
0.8222	Intermediate Similarity	NPC472869
0.8211	Intermediate Similarity	NPC456
0.8211	Intermediate Similarity	NPC472941
0.8211	Intermediate Similarity	NPC29952
0.8202	Intermediate Similarity	NPC96095
0.82	Intermediate Similarity	NPC475294
0.8182	Intermediate Similarity	NPC200513
0.8182	Intermediate Similarity	NPC472868
0.8172	Intermediate Similarity	NPC472978
0.8172	Intermediate Similarity	NPC473986
0.8172	Intermediate Similarity	NPC474018
0.8163	Intermediate Similarity	NPC40918
0.8161	Intermediate Similarity	NPC104545
0.8161	Intermediate Similarity	NPC37038
0.8161	Intermediate Similarity	NPC26139
0.8152	Intermediate Similarity	NPC36668
0.8152	Intermediate Similarity	NPC184663
0.8152	Intermediate Similarity	NPC284561
0.8152	Intermediate Similarity	NPC477973
0.8152	Intermediate Similarity	NPC118011
0.8152	Intermediate Similarity	NPC472973
0.8144	Intermediate Similarity	NPC471413
0.8144	Intermediate Similarity	NPC287833
0.814	Intermediate Similarity	NPC74410
0.8132	Intermediate Similarity	NPC231599
0.8125	Intermediate Similarity	NPC476253
0.8125	Intermediate Similarity	NPC474343
0.8125	Intermediate Similarity	NPC473456
0.8118	Intermediate Similarity	NPC180886
0.8111	Intermediate Similarity	NPC474537
0.8111	Intermediate Similarity	NPC29447
0.8105	Intermediate Similarity	NPC209355
0.8095	Intermediate Similarity	NPC20025
0.809	Intermediate Similarity	NPC97913
0.809	Intermediate Similarity	NPC105803
0.8085	Intermediate Similarity	NPC151722
0.8085	Intermediate Similarity	NPC472303
0.8085	Intermediate Similarity	NPC139692
0.8081	Intermediate Similarity	NPC476889
0.8068	Intermediate Similarity	NPC327002
0.8068	Intermediate Similarity	NPC221647
0.8065	Intermediate Similarity	NPC471818
0.8065	Intermediate Similarity	NPC472866
0.8065	Intermediate Similarity	NPC101651
0.8065	Intermediate Similarity	NPC159748
0.8061	Intermediate Similarity	NPC471412
0.8061	Intermediate Similarity	NPC93744
0.8061	Intermediate Similarity	NPC115862
0.8061	Intermediate Similarity	NPC476888
0.8046	Intermediate Similarity	NPC263951
0.8046	Intermediate Similarity	NPC231431
0.8043	Intermediate Similarity	NPC117122
0.8043	Intermediate Similarity	NPC472302
0.8043	Intermediate Similarity	NPC24816
0.8043	Intermediate Similarity	NPC104560
0.8041	Intermediate Similarity	NPC316598
0.8041	Intermediate Similarity	NPC98868
0.8041	Intermediate Similarity	NPC57079
0.8041	Intermediate Similarity	NPC478056
0.8041	Intermediate Similarity	NPC108368
0.8022	Intermediate Similarity	NPC324063
0.8022	Intermediate Similarity	NPC73038
0.8021	Intermediate Similarity	NPC269492
0.8	Intermediate Similarity	NPC248758
0.8	Intermediate Similarity	NPC84893
0.8	Intermediate Similarity	NPC65650
0.8	Intermediate Similarity	NPC472977
0.8	Intermediate Similarity	NPC156981
0.8	Intermediate Similarity	NPC19849
0.8	Intermediate Similarity	NPC164577
0.8	Intermediate Similarity	NPC118911
0.8	Intermediate Similarity	NPC472864
0.8	Intermediate Similarity	NPC472865
0.8	Intermediate Similarity	NPC91010
0.8	Intermediate Similarity	NPC472976
0.7981	Intermediate Similarity	NPC147180
0.7981	Intermediate Similarity	NPC264634
0.798	Intermediate Similarity	NPC476769
0.798	Intermediate Similarity	NPC475320
0.798	Intermediate Similarity	NPC476890
0.798	Intermediate Similarity	NPC162973
0.7979	Intermediate Similarity	NPC477783
0.7979	Intermediate Similarity	NPC472814
0.7979	Intermediate Similarity	NPC177037
0.7979	Intermediate Similarity	NPC303697
0.7979	Intermediate Similarity	NPC204341
0.7979	Intermediate Similarity	NPC289479
0.7978	Intermediate Similarity	NPC320514
0.7959	Intermediate Similarity	NPC117685
0.7959	Intermediate Similarity	NPC54705
0.7959	Intermediate Similarity	NPC51370
0.7957	Intermediate Similarity	NPC168131
0.7957	Intermediate Similarity	NPC281524
0.7957	Intermediate Similarity	NPC66344
0.7955	Intermediate Similarity	NPC477057
0.7955	Intermediate Similarity	NPC476809
0.7955	Intermediate Similarity	NPC2482
0.7938	Intermediate Similarity	NPC254496
0.7938	Intermediate Similarity	NPC285513
0.7938	Intermediate Similarity	NPC84335
0.7938	Intermediate Similarity	NPC38530
0.7935	Intermediate Similarity	NPC128644
0.7935	Intermediate Similarity	NPC181327
0.7935	Intermediate Similarity	NPC171722
0.7931	Intermediate Similarity	NPC260385
0.7931	Intermediate Similarity	NPC471409
0.7931	Intermediate Similarity	NPC59436
0.7931	Intermediate Similarity	NPC280654
0.7931	Intermediate Similarity	NPC275494
0.7931	Intermediate Similarity	NPC62336
0.7931	Intermediate Similarity	NPC239098
0.7931	Intermediate Similarity	NPC110094
0.7931	Intermediate Similarity	NPC179028
0.7921	Intermediate Similarity	NPC472935
0.7917	Intermediate Similarity	NPC295347
0.7917	Intermediate Similarity	NPC293052
0.7917	Intermediate Similarity	NPC476174
0.7912	Intermediate Similarity	NPC142649
0.7912	Intermediate Similarity	NPC311702
0.7912	Intermediate Similarity	NPC6185
0.7912	Intermediate Similarity	NPC8571
0.7912	Intermediate Similarity	NPC30984
0.7912	Intermediate Similarity	NPC123319
0.7912	Intermediate Similarity	NPC94531
0.7912	Intermediate Similarity	NPC476426
0.7912	Intermediate Similarity	NPC473038
0.7912	Intermediate Similarity	NPC241512
0.7907	Intermediate Similarity	NPC40353
0.7905	Intermediate Similarity	NPC159333
0.79	Intermediate Similarity	NPC478057
0.79	Intermediate Similarity	NPC112009
0.79	Intermediate Similarity	NPC180204
0.7895	Intermediate Similarity	NPC263780
0.7895	Intermediate Similarity	NPC214756
0.7895	Intermediate Similarity	NPC272075
0.7895	Intermediate Similarity	NPC295643
0.7895	Intermediate Similarity	NPC115021
0.7889	Intermediate Similarity	NPC200752
0.7882	Intermediate Similarity	NPC283908
0.7882	Intermediate Similarity	NPC183503
0.7882	Intermediate Similarity	NPC161923
0.7882	Intermediate Similarity	NPC103958
0.7882	Intermediate Similarity	NPC166797
0.7879	Intermediate Similarity	NPC63249
0.7879	Intermediate Similarity	NPC310981
0.7872	Intermediate Similarity	NPC477782
0.7865	Intermediate Similarity	NPC274050
0.7865	Intermediate Similarity	NPC477372
0.7865	Intermediate Similarity	NPC162632
0.7865	Intermediate Similarity	NPC147066
0.7865	Intermediate Similarity	NPC267691

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 NPC476369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1428
0.2-0.3	3619
0.3-0.4	2512
0.4-0.5	916
0.5-0.6	250
0.6-0.7	151
0.7-0.8	99
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4695	Discontinued
0.7857	Intermediate Similarity	NPD5696	Approved
0.7835	Intermediate Similarity	NPD7614	Phase 1
0.7812	Intermediate Similarity	NPD7748	Approved
0.7789	Intermediate Similarity	NPD7515	Phase 2
0.7789	Intermediate Similarity	NPD5693	Phase 1
0.7755	Intermediate Similarity	NPD6084	Phase 2
0.7755	Intermediate Similarity	NPD6083	Phase 2
0.7742	Intermediate Similarity	NPD3573	Approved
0.766	Intermediate Similarity	NPD5737	Approved
0.766	Intermediate Similarity	NPD6672	Approved
0.7653	Intermediate Similarity	NPD7732	Phase 3
0.7634	Intermediate Similarity	NPD7334	Approved
0.7634	Intermediate Similarity	NPD4623	Approved
0.7634	Intermediate Similarity	NPD6684	Approved
0.7634	Intermediate Similarity	NPD7521	Approved
0.7634	Intermediate Similarity	NPD5330	Approved
0.7634	Intermediate Similarity	NPD6409	Approved
0.7634	Intermediate Similarity	NPD7146	Approved
0.7634	Intermediate Similarity	NPD4519	Discontinued
0.7582	Intermediate Similarity	NPD4223	Phase 3
0.7582	Intermediate Similarity	NPD4221	Approved
0.7579	Intermediate Similarity	NPD6673	Approved
0.7579	Intermediate Similarity	NPD6080	Approved
0.7579	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6904	Approved
0.7576	Intermediate Similarity	NPD7902	Approved
0.7551	Intermediate Similarity	NPD5695	Phase 3
0.7551	Intermediate Similarity	NPD4629	Approved
0.7551	Intermediate Similarity	NPD5210	Approved
0.7527	Intermediate Similarity	NPD5329	Approved
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD7638	Approved
0.7474	Intermediate Similarity	NPD6903	Approved
0.7474	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6899	Approved
0.7429	Intermediate Similarity	NPD6881	Approved
0.7429	Intermediate Similarity	NPD6686	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.7423	Intermediate Similarity	NPD6079	Approved
0.7423	Intermediate Similarity	NPD5284	Approved
0.7423	Intermediate Similarity	NPD5281	Approved
0.7419	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD3666	Approved
0.7419	Intermediate Similarity	NPD4197	Approved
0.7404	Intermediate Similarity	NPD7128	Approved
0.7404	Intermediate Similarity	NPD6402	Approved
0.7404	Intermediate Similarity	NPD5739	Approved
0.7404	Intermediate Similarity	NPD6675	Approved
0.7396	Intermediate Similarity	NPD4753	Phase 2
0.7396	Intermediate Similarity	NPD5328	Approved
0.7374	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7115	Discovery
0.734	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD5697	Approved
0.7292	Intermediate Similarity	NPD5208	Approved
0.729	Intermediate Similarity	NPD7102	Approved
0.729	Intermediate Similarity	NPD7290	Approved
0.729	Intermediate Similarity	NPD6883	Approved
0.7273	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6011	Approved
0.7264	Intermediate Similarity	NPD7320	Approved
0.7263	Intermediate Similarity	NPD3618	Phase 1
0.7263	Intermediate Similarity	NPD5205	Approved
0.7263	Intermediate Similarity	NPD4693	Phase 3
0.7263	Intermediate Similarity	NPD4688	Approved
0.7263	Intermediate Similarity	NPD5690	Phase 2
0.7263	Intermediate Similarity	NPD4689	Approved
0.7263	Intermediate Similarity	NPD4138	Approved
0.7263	Intermediate Similarity	NPD6098	Approved
0.7263	Intermediate Similarity	NPD4690	Approved
0.7245	Intermediate Similarity	NPD6050	Approved
0.7234	Intermediate Similarity	NPD4786	Approved
0.7222	Intermediate Similarity	NPD6650	Approved
0.7222	Intermediate Similarity	NPD8130	Phase 1
0.7222	Intermediate Similarity	NPD6847	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD6617	Approved
0.7222	Intermediate Similarity	NPD6869	Approved
0.7204	Intermediate Similarity	NPD3667	Approved
0.7196	Intermediate Similarity	NPD6012	Approved
0.7196	Intermediate Similarity	NPD6014	Approved
0.7196	Intermediate Similarity	NPD6372	Approved
0.7196	Intermediate Similarity	NPD6013	Approved
0.7196	Intermediate Similarity	NPD6373	Approved
0.717	Intermediate Similarity	NPD5701	Approved
0.7157	Intermediate Similarity	NPD4225	Approved
0.7156	Intermediate Similarity	NPD8297	Approved
0.7156	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD5785	Approved
0.7129	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5222	Approved
0.7129	Intermediate Similarity	NPD5221	Approved
0.7115	Intermediate Similarity	NPD5211	Phase 2
0.7087	Intermediate Similarity	NPD5285	Approved
0.7087	Intermediate Similarity	NPD5286	Approved
0.7087	Intermediate Similarity	NPD4696	Approved
0.7083	Intermediate Similarity	NPD4694	Approved
0.7083	Intermediate Similarity	NPD5280	Approved
0.7083	Intermediate Similarity	NPD5279	Phase 3
0.7071	Intermediate Similarity	NPD6411	Approved
0.7071	Intermediate Similarity	NPD5694	Approved
0.7065	Intermediate Similarity	NPD4195	Approved
0.7064	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7331	Phase 2
0.7059	Intermediate Similarity	NPD5173	Approved
0.7059	Intermediate Similarity	NPD4755	Approved
0.7041	Intermediate Similarity	NPD6051	Approved
0.7019	Intermediate Similarity	NPD5223	Approved
0.7009	Intermediate Similarity	NPD6614	Approved
0.7	Intermediate Similarity	NPD8039	Approved
0.7	Intermediate Similarity	NPD4202	Approved
0.6981	Remote Similarity	NPD5141	Approved
0.697	Remote Similarity	NPD5207	Approved
0.6961	Remote Similarity	NPD4697	Phase 3
0.6952	Remote Similarity	NPD5224	Approved
0.6952	Remote Similarity	NPD5225	Approved
0.6952	Remote Similarity	NPD5091	Approved
0.6952	Remote Similarity	NPD4633	Approved
0.6952	Remote Similarity	NPD5226	Approved
0.6947	Remote Similarity	NPD4788	Approved
0.6941	Remote Similarity	NPD7341	Phase 2
0.6937	Remote Similarity	NPD4632	Approved
0.6932	Remote Similarity	NPD4691	Approved
0.6931	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD6404	Discontinued
0.6923	Remote Similarity	NPD4700	Approved
0.6887	Remote Similarity	NPD5175	Approved
0.6887	Remote Similarity	NPD5174	Approved
0.6881	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3668	Phase 3
0.6869	Remote Similarity	NPD6101	Approved
0.6869	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6335	Approved
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD4137	Phase 3
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6868	Approved
0.6814	Remote Similarity	NPD6274	Approved
0.68	Remote Similarity	NPD4096	Approved
0.6792	Remote Similarity	NPD7632	Discontinued
0.6783	Remote Similarity	NPD7100	Approved
0.6783	Remote Similarity	NPD7101	Approved
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6008	Approved
0.6754	Remote Similarity	NPD6009	Approved
0.6754	Remote Similarity	NPD6317	Approved
0.6742	Remote Similarity	NPD4747	Approved
0.6729	Remote Similarity	NPD6052	Approved
0.6729	Remote Similarity	NPD4754	Approved
0.6703	Remote Similarity	NPD4058	Approved
0.6699	Remote Similarity	NPD5654	Approved
0.6697	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD6313	Approved
0.6696	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6634	Remote Similarity	NPD6698	Approved
0.6634	Remote Similarity	NPD46	Approved
0.6633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5363	Approved
0.6606	Remote Similarity	NPD4768	Approved
0.6606	Remote Similarity	NPD4767	Approved
0.66	Remote Similarity	NPD4518	Approved
0.6585	Remote Similarity	NPD7260	Phase 2
0.6583	Remote Similarity	NPD7507	Approved
0.6581	Remote Similarity	NPD6319	Approved
0.6571	Remote Similarity	NPD5959	Approved
0.6569	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6562	Remote Similarity	NPD4692	Approved
0.6562	Remote Similarity	NPD4139	Approved
0.6555	Remote Similarity	NPD7604	Phase 2
0.6545	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6909	Approved
0.6525	Remote Similarity	NPD5983	Phase 2
0.6525	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6908	Approved
0.6522	Remote Similarity	NPD5733	Approved
0.6518	Remote Similarity	NPD5249	Phase 3
0.6518	Remote Similarity	NPD5135	Approved
0.6518	Remote Similarity	NPD5251	Approved
0.6518	Remote Similarity	NPD5250	Approved
0.6518	Remote Similarity	NPD4634	Approved
0.6518	Remote Similarity	NPD6371	Approved
0.6518	Remote Similarity	NPD5169	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