NPASS Compound

Structure

NPC131813 OpenBabel07101718322D 24 26 0 0 1 0 0 0 0 0999 V2000 3.3147 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7788 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 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 4.1808 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9128 -0.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7788 0.6636 0.0000 C 0 0 1 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 5.0468 -0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7788 -0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7788 -2.0685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6449 1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 1.7796 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 7 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 15 19 1 6 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	3.04
LogD:	3.333
LogS:	-3.809
# Rotatable Bonds:	4
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	4.542
Fsp3:	0.7
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:	-4.909
MDCK Permeability:	1.6084004528238438e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.614
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.668

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.345
Plasma Protein Binding (PPB):	90.58890533447266%
Volume Distribution (VD):	0.935
Pgp-substrate:	10.074369430541992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.642
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	10.559
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.392
Carcinogencity:	0.224
Eye Corrosion:	0.009
Eye Irritation:	0.285
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: NPC131813

Natural Product ID:	NPC131813
*Common Name:**	3Beta,18-Dihydroxylabda-8(17),13-Dien-15,16-Olide
IUPAC Name:	3-[2-[(1S,4aR,5R,6S,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	KKFRLYZLIKHVCA-NDLGOLERSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-13-4-7-16-19(2,9-8-17(22)20(16,3)12-21)15(13)6-5-14-10-18(23)24-11-14/h10,15-17,21-22H,1,4-9,11-12H2,2-3H3/t15-,16+,17-,19+,20-/m0/s1
SMILES:	C=C1CC[C@@H]2[C@](C)(CC[C@@H]([C@@]2(C)CO)O)[C@H]1CCC1=CC(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333385
PubChem CID:	71576915
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
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23394284]
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31457	Amomum kravanh	Species	Zingiberaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	10.0	%	PMID[468697]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	90.0	%	PMID[468697]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	58900.0	nM	PMID[468697]

☑ 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 NPC131813 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	1113
0.2-0.3	4068
0.3-0.4	9877
0.4-0.5	12739
0.5-0.6	6590
0.6-0.7	5785
0.7-0.8	2030
0.8-0.85	205
0.85-0.9	85
0.9-0.95	25
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC78973
0.9383	High Similarity	NPC311070
0.9302	High Similarity	NPC205034
0.9302	High Similarity	NPC139692
0.9302	High Similarity	NPC162615
0.9302	High Similarity	NPC472812
0.9302	High Similarity	NPC152778
0.9186	High Similarity	NPC472811
0.9186	High Similarity	NPC72845
0.9091	High Similarity	NPC276110
0.908	High Similarity	NPC53555
0.907	High Similarity	NPC310479
0.907	High Similarity	NPC221111
0.907	High Similarity	NPC280149
0.9059	High Similarity	NPC472810
0.9059	High Similarity	NPC472809
0.8989	High Similarity	NPC16967
0.8989	High Similarity	NPC242848
0.8989	High Similarity	NPC134072
0.8989	High Similarity	NPC234993
0.8977	High Similarity	NPC105490
0.8977	High Similarity	NPC191521
0.8966	High Similarity	NPC329842
0.8941	High Similarity	NPC166857
0.8929	High Similarity	NPC474013
0.8916	High Similarity	NPC79945
0.8902	High Similarity	NPC170303
0.8889	High Similarity	NPC51499
0.8876	High Similarity	NPC472441
0.8864	High Similarity	NPC7349
0.8851	High Similarity	NPC182136
0.8837	High Similarity	NPC93411
0.881	High Similarity	NPC96055
0.8791	High Similarity	NPC474440
0.8791	High Similarity	NPC275086
0.8791	High Similarity	NPC325229
0.8791	High Similarity	NPC278673
0.878	High Similarity	NPC281880
0.8778	High Similarity	NPC473153
0.8764	High Similarity	NPC470255
0.8764	High Similarity	NPC57117
0.8736	High Similarity	NPC50488
0.8736	High Similarity	NPC470734
0.8736	High Similarity	NPC474396
0.8721	High Similarity	NPC473891
0.8696	High Similarity	NPC38855
0.869	High Similarity	NPC476927
0.869	High Similarity	NPC42476
0.8681	High Similarity	NPC73911
0.8675	High Similarity	NPC159148
0.8652	High Similarity	NPC472640
0.8652	High Similarity	NPC472641
0.8642	High Similarity	NPC189206
0.8636	High Similarity	NPC472642
0.8605	High Similarity	NPC329692
0.8602	High Similarity	NPC11974
0.8588	High Similarity	NPC32223
0.8587	High Similarity	NPC124512
0.8587	High Similarity	NPC278386
0.8587	High Similarity	NPC159763
0.8571	High Similarity	NPC256112
0.8571	High Similarity	NPC165632
0.8571	High Similarity	NPC2524
0.8571	High Similarity	NPC471218
0.8556	High Similarity	NPC469697
0.8539	High Similarity	NPC472814
0.8539	High Similarity	NPC177037
0.8523	High Similarity	NPC82876
0.8523	High Similarity	NPC174342
0.8511	High Similarity	NPC472815
0.8511	High Similarity	NPC475038
0.8511	High Similarity	NPC109195
0.8511	High Similarity	NPC476081
0.8495	Intermediate Similarity	NPC476299
0.8495	Intermediate Similarity	NPC117685
0.8495	Intermediate Similarity	NPC324841
0.8495	Intermediate Similarity	NPC474012
0.8495	Intermediate Similarity	NPC16601
0.8488	Intermediate Similarity	NPC471795
0.8488	Intermediate Similarity	NPC65661
0.8488	Intermediate Similarity	NPC30984
0.8488	Intermediate Similarity	NPC86316
0.8488	Intermediate Similarity	NPC476602
0.8488	Intermediate Similarity	NPC106416
0.8478	Intermediate Similarity	NPC231751
0.8471	Intermediate Similarity	NPC472377
0.8452	Intermediate Similarity	NPC475944
0.8444	Intermediate Similarity	NPC110022
0.8427	Intermediate Similarity	NPC51486
0.8421	Intermediate Similarity	NPC112009
0.8421	Intermediate Similarity	NPC97487
0.8421	Intermediate Similarity	NPC471938
0.8421	Intermediate Similarity	NPC189588
0.8421	Intermediate Similarity	NPC10232
0.8421	Intermediate Similarity	NPC45897
0.8421	Intermediate Similarity	NPC196471
0.8421	Intermediate Similarity	NPC120321
0.8421	Intermediate Similarity	NPC187302
0.8409	Intermediate Similarity	NPC472378
0.8409	Intermediate Similarity	NPC474629
0.8409	Intermediate Similarity	NPC104560
0.8404	Intermediate Similarity	NPC25177
0.8404	Intermediate Similarity	NPC303559
0.8404	Intermediate Similarity	NPC247701
0.8404	Intermediate Similarity	NPC471412
0.8404	Intermediate Similarity	NPC268829
0.8404	Intermediate Similarity	NPC222875
0.8404	Intermediate Similarity	NPC295110
0.8391	Intermediate Similarity	NPC175145
0.8391	Intermediate Similarity	NPC475069
0.8391	Intermediate Similarity	NPC471219
0.8387	Intermediate Similarity	NPC473154
0.8372	Intermediate Similarity	NPC306951
0.8372	Intermediate Similarity	NPC102048
0.837	Intermediate Similarity	NPC88009
0.837	Intermediate Similarity	NPC162346
0.8353	Intermediate Similarity	NPC155521
0.8352	Intermediate Similarity	NPC201725
0.8352	Intermediate Similarity	NPC298973
0.8352	Intermediate Similarity	NPC140277
0.8352	Intermediate Similarity	NPC104925
0.8333	Intermediate Similarity	NPC78594
0.8333	Intermediate Similarity	NPC10636
0.8333	Intermediate Similarity	NPC469802
0.8333	Intermediate Similarity	NPC471937
0.8316	Intermediate Similarity	NPC471914
0.8316	Intermediate Similarity	NPC114540
0.8316	Intermediate Similarity	NPC32577
0.8316	Intermediate Similarity	NPC155332
0.8315	Intermediate Similarity	NPC5509
0.8313	Intermediate Similarity	NPC184737
0.8298	Intermediate Similarity	NPC471413
0.8298	Intermediate Similarity	NPC474190
0.8298	Intermediate Similarity	NPC251680
0.8298	Intermediate Similarity	NPC201406
0.8295	Intermediate Similarity	NPC471796
0.828	Intermediate Similarity	NPC474343
0.828	Intermediate Similarity	NPC210337
0.828	Intermediate Similarity	NPC253826
0.828	Intermediate Similarity	NPC477719
0.828	Intermediate Similarity	NPC475709
0.828	Intermediate Similarity	NPC477718
0.8276	Intermediate Similarity	NPC35933
0.8276	Intermediate Similarity	NPC473251
0.8276	Intermediate Similarity	NPC42586
0.8261	Intermediate Similarity	NPC471915
0.8261	Intermediate Similarity	NPC183012
0.8261	Intermediate Similarity	NPC111273
0.8256	Intermediate Similarity	NPC474809
0.8256	Intermediate Similarity	NPC474193
0.8256	Intermediate Similarity	NPC12283
0.8247	Intermediate Similarity	NPC220217
0.8247	Intermediate Similarity	NPC34768
0.8247	Intermediate Similarity	NPC119855
0.8242	Intermediate Similarity	NPC38232
0.8242	Intermediate Similarity	NPC472303
0.8242	Intermediate Similarity	NPC115021
0.8235	Intermediate Similarity	NPC142163
0.8229	Intermediate Similarity	NPC180204
0.8229	Intermediate Similarity	NPC297617
0.8229	Intermediate Similarity	NPC160583
0.8229	Intermediate Similarity	NPC281378
0.8229	Intermediate Similarity	NPC472821
0.8229	Intermediate Similarity	NPC120009
0.8222	Intermediate Similarity	NPC477782
0.8214	Intermediate Similarity	NPC242767
0.8211	Intermediate Similarity	NPC472554
0.8211	Intermediate Similarity	NPC473160
0.8202	Intermediate Similarity	NPC106332
0.8202	Intermediate Similarity	NPC291665
0.8193	Intermediate Similarity	NPC283619
0.8191	Intermediate Similarity	NPC218107
0.8191	Intermediate Similarity	NPC108368
0.8191	Intermediate Similarity	NPC92275
0.8191	Intermediate Similarity	NPC57079
0.8182	Intermediate Similarity	NPC474970
0.8172	Intermediate Similarity	NPC475380
0.8172	Intermediate Similarity	NPC194132
0.8172	Intermediate Similarity	NPC209297
0.8172	Intermediate Similarity	NPC190713
0.8172	Intermediate Similarity	NPC202833
0.8163	Intermediate Similarity	NPC471205
0.8163	Intermediate Similarity	NPC187435
0.8163	Intermediate Similarity	NPC475074
0.8163	Intermediate Similarity	NPC67321
0.8163	Intermediate Similarity	NPC179380
0.8161	Intermediate Similarity	NPC471302
0.814	Intermediate Similarity	NPC200513
0.8132	Intermediate Similarity	NPC289479
0.8132	Intermediate Similarity	NPC234335
0.8132	Intermediate Similarity	NPC477783
0.8125	Intermediate Similarity	NPC283343
0.8125	Intermediate Similarity	NPC273668
0.8125	Intermediate Similarity	NPC11956
0.8125	Intermediate Similarity	NPC472552
0.8125	Intermediate Similarity	NPC162973
0.8125	Intermediate Similarity	NPC121423
0.8125	Intermediate Similarity	NPC258547
0.8118	Intermediate Similarity	NPC268827
0.8111	Intermediate Similarity	NPC262858

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 NPC131813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1352
0.2-0.3	3741
0.3-0.4	2586
0.4-0.5	857
0.5-0.6	209
0.6-0.7	212
0.7-0.8	40
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD4225	Approved
0.8387	Intermediate Similarity	NPD7638	Approved
0.8298	Intermediate Similarity	NPD7640	Approved
0.8298	Intermediate Similarity	NPD7639	Approved
0.814	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7748	Approved
0.7576	Intermediate Similarity	NPD7632	Discontinued
0.7553	Intermediate Similarity	NPD7515	Phase 2
0.7549	Intermediate Similarity	NPD6686	Approved
0.7476	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7327	Approved
0.7407	Intermediate Similarity	NPD7328	Approved
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7386	Intermediate Similarity	NPD7645	Phase 2
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7347	Intermediate Similarity	NPD7902	Approved
0.734	Intermediate Similarity	NPD6051	Approved
0.7339	Intermediate Similarity	NPD7516	Approved
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7303	Intermediate Similarity	NPD7525	Registered
0.73	Intermediate Similarity	NPD5344	Discontinued
0.7283	Intermediate Similarity	NPD1694	Approved
0.7282	Intermediate Similarity	NPD5701	Approved
0.7282	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD8294	Approved
0.7273	Intermediate Similarity	NPD8377	Approved
0.7238	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7320	Approved
0.7212	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7207	Intermediate Similarity	NPD8380	Approved
0.7207	Intermediate Similarity	NPD8335	Approved
0.7207	Intermediate Similarity	NPD8379	Approved
0.7207	Intermediate Similarity	NPD8378	Approved
0.7207	Intermediate Similarity	NPD8296	Approved
0.7207	Intermediate Similarity	NPD8033	Approved
0.7188	Intermediate Similarity	NPD7637	Suspended
0.7172	Intermediate Similarity	NPD6084	Phase 2
0.7172	Intermediate Similarity	NPD6083	Phase 2
0.7158	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7113	Intermediate Similarity	NPD6399	Phase 3
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7065	Intermediate Similarity	NPD6695	Phase 3
0.7048	Intermediate Similarity	NPD6011	Approved
0.7045	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7900	Approved
0.703	Intermediate Similarity	NPD6648	Approved
0.7021	Intermediate Similarity	NPD7521	Approved
0.7021	Intermediate Similarity	NPD7334	Approved
0.7021	Intermediate Similarity	NPD7146	Approved
0.7021	Intermediate Similarity	NPD6684	Approved
0.7021	Intermediate Similarity	NPD6409	Approved
0.7021	Intermediate Similarity	NPD5330	Approved
0.701	Intermediate Similarity	NPD6079	Approved
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD3133	Approved
0.6989	Remote Similarity	NPD3665	Phase 1
0.6989	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3666	Approved
0.697	Remote Similarity	NPD5695	Phase 3
0.6957	Remote Similarity	NPD7507	Approved
0.6957	Remote Similarity	NPD3667	Approved
0.6952	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6939	Remote Similarity	NPD4202	Approved
0.6932	Remote Similarity	NPD7339	Approved
0.6932	Remote Similarity	NPD6942	Approved
0.6931	Remote Similarity	NPD5696	Approved
0.6915	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7503	Approved
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4697	Phase 3
0.6893	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6903	Approved
0.6867	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5285	Approved
0.6863	Remote Similarity	NPD5286	Approved
0.6863	Remote Similarity	NPD4700	Approved
0.6863	Remote Similarity	NPD4696	Approved
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5693	Phase 1
0.6837	Remote Similarity	NPD8035	Phase 2
0.6837	Remote Similarity	NPD8034	Phase 2
0.6837	Remote Similarity	NPD6411	Approved
0.6832	Remote Similarity	NPD5173	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.6813	Remote Similarity	NPD6929	Approved
0.6809	Remote Similarity	NPD4786	Approved
0.6804	Remote Similarity	NPD4753	Phase 2
0.68	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7319	Approved
0.6771	Remote Similarity	NPD7750	Discontinued
0.6771	Remote Similarity	NPD7524	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6768	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD5778	Approved
0.6762	Remote Similarity	NPD5141	Approved
0.6757	Remote Similarity	NPD6274	Approved
0.6742	Remote Similarity	NPD8264	Approved
0.6739	Remote Similarity	NPD6930	Phase 2
0.6739	Remote Similarity	NPD6931	Approved
0.6737	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5785	Approved
0.6735	Remote Similarity	NPD7838	Discovery
0.6735	Remote Similarity	NPD46	Approved
0.6735	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD4633	Approved
0.6731	Remote Similarity	NPD5224	Approved
0.6731	Remote Similarity	NPD5225	Approved
0.6731	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6635	Remote Similarity	NPD5223	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6101	Approved
0.663	Remote Similarity	NPD4195	Approved
0.6607	Remote Similarity	NPD6868	Approved
0.6602	Remote Similarity	NPD5290	Discontinued
0.6598	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5209	Approved
0.6593	Remote Similarity	NPD6925	Approved
0.6593	Remote Similarity	NPD5776	Phase 2
0.6591	Remote Similarity	NPD7150	Approved
0.6591	Remote Similarity	NPD7151	Approved
0.6591	Remote Similarity	NPD7152	Approved
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6577	Remote Similarity	NPD4632	Approved
0.6559	Remote Similarity	NPD7332	Phase 2
0.6559	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4695	Discontinued
0.6559	Remote Similarity	NPD7514	Phase 3
0.6559	Remote Similarity	NPD7509	Discontinued
0.6552	Remote Similarity	NPD6922	Approved
0.6552	Remote Similarity	NPD6923	Approved
0.6549	Remote Similarity	NPD6317	Approved
0.6542	Remote Similarity	NPD4767	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD4768	Approved
0.6526	Remote Similarity	NPD7154	Phase 3
0.6522	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6319	Approved
0.6522	Remote Similarity	NPD7145	Approved
0.6522	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4754	Approved
0.65	Remote Similarity	NPD7087	Discontinued
0.6495	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4623	Approved
0.6495	Remote Similarity	NPD4519	Discontinued
0.6491	Remote Similarity	NPD6335	Approved
0.6491	Remote Similarity	NPD6313	Approved
0.6491	Remote Similarity	NPD6314	Approved
0.6489	Remote Similarity	NPD6902	Approved
0.6486	Remote Similarity	NPD6053	Discontinued
0.6481	Remote Similarity	NPD6412	Phase 2
0.6477	Remote Similarity	NPD7144	Approved
0.6477	Remote Similarity	NPD7143	Approved
0.6476	Remote Similarity	NPD4159	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6465	Remote Similarity	NPD6904	Approved
0.6465	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD6080	Approved
0.6458	Remote Similarity	NPD3668	Phase 3
0.6422	Remote Similarity	NPD4729	Approved
0.6422	Remote Similarity	NPD4730	Approved
0.6422	Remote Similarity	NPD5128	Approved
0.6422	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4221	Approved
0.6421	Remote Similarity	NPD4223	Phase 3

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