NPASS Compound

Structure

CID12854 OpenBabel06191715342D 25 28 0 0 1 0 0 0 0 0999 V2000 3.2612 -2.1223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8281 -1.1705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4539 0.1762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6036 -1.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7055 -1.7055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0962 -4.0413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5613 -4.6988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2412 -0.4955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0427 -2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9620 -4.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0479 -1.0479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1445 -3.1431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9299 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4595 -4.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7002 -3.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4955 -1.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1705 -1.8281 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9299 -0.9299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3914 -2.1653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0687 -2.0687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6575 0.6575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2394 -4.9646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6288 -3.5113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 24 1 0 0 0 0 10 25 1 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 6 0 0 0 17 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 6 0 0 0 20 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	345.746
LogP:	3.125
LogD:	2.622
LogS:	-4.185
# Rotatable Bonds:	5
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.818
Synthetic Accessibility Score:	4.482
Fsp3:	0.3
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:	-4.797
MDCK Permeability:	1.7311725969193503e-05
Pgp-inhibitor:	0.817
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	99.89840698242188%
Volume Distribution (VD):	0.805
Pgp-substrate:	1.6046080589294434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.504
CYP1A2-substrate:	0.748
CYP2C19-inhibitor:	0.853
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	10.283
Half-life (T1/2):	0.39

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.43
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.942
Carcinogencity:	0.321
Eye Corrosion:	0.003
Eye Irritation:	0.521
Respiratory Toxicity:	0.779

Download Data

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

Natural Product: NPC12854

Natural Product ID:	NPC12854
*Common Name:**	Piperkadsin C
IUPAC Name:	(1R,6S)-6-[(R)-1,3-benzodioxol-5-yl(hydroxy)methyl]-7-methoxy-6-methyl-3-prop-2-enylbicyclo[3.1.1]hepta-3,5(7)-dien-2-one
Synonyms:	Piperkadsin C
Standard InCHIKey:	NOXNHMNKQIHADP-PWIZWCRZSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-4-5-11-8-13-18(23-3)16(17(11)21)20(13,2)19(22)12-6-7-14-15(9-12)25-10-24-14/h4,6-9,16,19,22H,1,5,10H2,2-3H3/t16-,19+,20+/m0/s1
SMILES:	C=CCC1=CC2=C([C@H](C1=O)[C@]2(C)[C@@H](c1ccc2c(c1)OCO2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL604682
PubChem CID:	46228396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11040054]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724856]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19900811]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8368081]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Inhibition	=	60.8	%	PMID[529399]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	14600.0	nM	PMID[529399]

☑ 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 NPC12854 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	342
0.1-0.2	1324
0.2-0.3	2902
0.3-0.4	6789
0.4-0.5	11609
0.5-0.6	4624
0.6-0.7	9724
0.7-0.8	5254
0.8-0.85	120
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8986	High Similarity	NPC476336
0.8966	High Similarity	NPC51681
0.8912	High Similarity	NPC15743
0.8824	High Similarity	NPC476364
0.8667	High Similarity	NPC472560
0.8552	High Similarity	NPC37065
0.8544	High Similarity	NPC476337
0.8543	High Similarity	NPC30890
0.8523	High Similarity	NPC104956
0.8514	High Similarity	NPC470855
0.8514	High Similarity	NPC322021
0.8503	High Similarity	NPC166184
0.85	High Similarity	NPC100420
0.8487	Intermediate Similarity	NPC476338
0.8487	Intermediate Similarity	NPC153620
0.8487	Intermediate Similarity	NPC25496
0.8487	Intermediate Similarity	NPC24257
0.8487	Intermediate Similarity	NPC476359
0.8481	Intermediate Similarity	NPC68619
0.8481	Intermediate Similarity	NPC475095
0.8452	Intermediate Similarity	NPC56184
0.8447	Intermediate Similarity	NPC474301
0.8428	Intermediate Similarity	NPC239818
0.8428	Intermediate Similarity	NPC218471
0.8421	Intermediate Similarity	NPC189054
0.8421	Intermediate Similarity	NPC3982
0.8403	Intermediate Similarity	NPC477694
0.8403	Intermediate Similarity	NPC477705
0.8395	Intermediate Similarity	NPC476277
0.8389	Intermediate Similarity	NPC278076
0.8365	Intermediate Similarity	NPC76211
0.8356	Intermediate Similarity	NPC327410
0.8355	Intermediate Similarity	NPC327052
0.8345	Intermediate Similarity	NPC477706
0.8333	Intermediate Similarity	NPC28398
0.8333	Intermediate Similarity	NPC151425
0.8323	Intermediate Similarity	NPC177830
0.8323	Intermediate Similarity	NPC475170
0.8322	Intermediate Similarity	NPC64948
0.8289	Intermediate Similarity	NPC46880
0.8289	Intermediate Similarity	NPC239608
0.8289	Intermediate Similarity	NPC46161
0.8288	Intermediate Similarity	NPC104077
0.8288	Intermediate Similarity	NPC219671
0.8288	Intermediate Similarity	NPC147616
0.8288	Intermediate Similarity	NPC259742
0.828	Intermediate Similarity	NPC308555
0.828	Intermediate Similarity	NPC245948
0.8278	Intermediate Similarity	NPC476842
0.8278	Intermediate Similarity	NPC52664
0.8278	Intermediate Similarity	NPC476840
0.8278	Intermediate Similarity	NPC46180
0.8276	Intermediate Similarity	NPC280399
0.8276	Intermediate Similarity	NPC233961
0.8276	Intermediate Similarity	NPC195292
0.8276	Intermediate Similarity	NPC142985
0.8276	Intermediate Similarity	NPC339621
0.8269	Intermediate Similarity	NPC62354
0.8267	Intermediate Similarity	NPC474784
0.8258	Intermediate Similarity	NPC477698
0.8243	Intermediate Similarity	NPC174191
0.8243	Intermediate Similarity	NPC470990
0.8239	Intermediate Similarity	NPC478055
0.8235	Intermediate Similarity	NPC223185
0.8228	Intermediate Similarity	NPC136757
0.8228	Intermediate Similarity	NPC25127
0.8221	Intermediate Similarity	NPC475738
0.8219	Intermediate Similarity	NPC469480
0.8217	Intermediate Similarity	NPC476335
0.8212	Intermediate Similarity	NPC100675
0.821	Intermediate Similarity	NPC476244
0.8205	Intermediate Similarity	NPC229882
0.8205	Intermediate Similarity	NPC158635
0.8204	Intermediate Similarity	NPC469438
0.8194	Intermediate Similarity	NPC304821
0.8187	Intermediate Similarity	NPC475663
0.8187	Intermediate Similarity	NPC286919
0.8176	Intermediate Similarity	NPC186316
0.8176	Intermediate Similarity	NPC254163
0.8176	Intermediate Similarity	NPC267242
0.817	Intermediate Similarity	NPC50696
0.8169	Intermediate Similarity	NPC244876
0.8165	Intermediate Similarity	NPC327225
0.8165	Intermediate Similarity	NPC245615
0.8165	Intermediate Similarity	NPC180388
0.8165	Intermediate Similarity	NPC61604
0.8165	Intermediate Similarity	NPC299706
0.8165	Intermediate Similarity	NPC115466
0.8163	Intermediate Similarity	NPC471505
0.8163	Intermediate Similarity	NPC106739
0.816	Intermediate Similarity	NPC469518
0.816	Intermediate Similarity	NPC469475
0.816	Intermediate Similarity	NPC100425
0.8153	Intermediate Similarity	NPC178048
0.8153	Intermediate Similarity	NPC164082
0.8148	Intermediate Similarity	NPC477627
0.8141	Intermediate Similarity	NPC472567
0.8141	Intermediate Similarity	NPC478242
0.8137	Intermediate Similarity	NPC469384
0.8137	Intermediate Similarity	NPC472565
0.8133	Intermediate Similarity	NPC14022
0.8125	Intermediate Similarity	NPC237946
0.8125	Intermediate Similarity	NPC32373
0.8117	Intermediate Similarity	NPC469683
0.8113	Intermediate Similarity	NPC60084
0.8113	Intermediate Similarity	NPC287504
0.811	Intermediate Similarity	NPC180586
0.8105	Intermediate Similarity	NPC86455
0.8105	Intermediate Similarity	NPC125134
0.8105	Intermediate Similarity	NPC472564
0.8105	Intermediate Similarity	NPC474966
0.8105	Intermediate Similarity	NPC137920
0.8101	Intermediate Similarity	NPC477699
0.8098	Intermediate Similarity	NPC125991
0.8092	Intermediate Similarity	NPC166137
0.8092	Intermediate Similarity	NPC82336
0.8092	Intermediate Similarity	NPC78987
0.8092	Intermediate Similarity	NPC323601
0.8092	Intermediate Similarity	NPC282291
0.8089	Intermediate Similarity	NPC205054
0.8086	Intermediate Similarity	NPC472961
0.8086	Intermediate Similarity	NPC472962
0.8079	Intermediate Similarity	NPC178290
0.8077	Intermediate Similarity	NPC1580
0.8075	Intermediate Similarity	NPC474990
0.8075	Intermediate Similarity	NPC207584
0.8075	Intermediate Similarity	NPC19947
0.8075	Intermediate Similarity	NPC40920
0.8075	Intermediate Similarity	NPC476340
0.8075	Intermediate Similarity	NPC223335
0.8069	Intermediate Similarity	NPC12022
0.8069	Intermediate Similarity	NPC293641
0.8069	Intermediate Similarity	NPC20287
0.8069	Intermediate Similarity	NPC20404
0.8067	Intermediate Similarity	NPC90431
0.8063	Intermediate Similarity	NPC38699
0.8063	Intermediate Similarity	NPC131532
0.8054	Intermediate Similarity	NPC45404
0.8054	Intermediate Similarity	NPC145769
0.8052	Intermediate Similarity	NPC474036
0.8052	Intermediate Similarity	NPC469615
0.805	Intermediate Similarity	NPC44730
0.8049	Intermediate Similarity	NPC475865
0.8047	Intermediate Similarity	NPC469397
0.8041	Intermediate Similarity	NPC239302
0.8038	Intermediate Similarity	NPC475311
0.8038	Intermediate Similarity	NPC477700
0.8038	Intermediate Similarity	NPC473680
0.8038	Intermediate Similarity	NPC234152
0.8038	Intermediate Similarity	NPC32079
0.8038	Intermediate Similarity	NPC473579
0.8038	Intermediate Similarity	NPC475454
0.8038	Intermediate Similarity	NPC31132
0.8038	Intermediate Similarity	NPC163002
0.8037	Intermediate Similarity	NPC288149
0.8036	Intermediate Similarity	NPC473467
0.8036	Intermediate Similarity	NPC475197
0.8036	Intermediate Similarity	NPC105137
0.8027	Intermediate Similarity	NPC215941
0.8027	Intermediate Similarity	NPC137427
0.8027	Intermediate Similarity	NPC311419
0.8027	Intermediate Similarity	NPC244246
0.8027	Intermediate Similarity	NPC65935
0.8027	Intermediate Similarity	NPC319282
0.8027	Intermediate Similarity	NPC275724
0.8027	Intermediate Similarity	NPC123196
0.8026	Intermediate Similarity	NPC147379
0.8025	Intermediate Similarity	NPC179914
0.8025	Intermediate Similarity	NPC62518
0.8025	Intermediate Similarity	NPC215375
0.8025	Intermediate Similarity	NPC145569
0.8025	Intermediate Similarity	NPC216223
0.8025	Intermediate Similarity	NPC469654
0.8025	Intermediate Similarity	NPC474903
0.8014	Intermediate Similarity	NPC278308
0.8013	Intermediate Similarity	NPC52968
0.8013	Intermediate Similarity	NPC231719
0.8013	Intermediate Similarity	NPC88345
0.8012	Intermediate Similarity	NPC163635
0.8012	Intermediate Similarity	NPC228357
0.8012	Intermediate Similarity	NPC471180
0.8012	Intermediate Similarity	NPC109765
0.8012	Intermediate Similarity	NPC188217
0.8012	Intermediate Similarity	NPC261090
0.8	Intermediate Similarity	NPC101624
0.8	Intermediate Similarity	NPC476841
0.8	Intermediate Similarity	NPC142547
0.8	Intermediate Similarity	NPC18576
0.8	Intermediate Similarity	NPC184938
0.8	Intermediate Similarity	NPC135777
0.8	Intermediate Similarity	NPC476843
0.8	Intermediate Similarity	NPC474158
0.8	Intermediate Similarity	NPC62051
0.7988	Intermediate Similarity	NPC475244
0.7988	Intermediate Similarity	NPC56735
0.7988	Intermediate Similarity	NPC76687
0.7988	Intermediate Similarity	NPC61594
0.7987	Intermediate Similarity	NPC28724
0.7987	Intermediate Similarity	NPC476434
0.7987	Intermediate Similarity	NPC203664

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 NPC12854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	850
0.2-0.3	1686
0.3-0.4	2623
0.4-0.5	2036
0.5-0.6	1047
0.6-0.7	543
0.7-0.8	62
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
0.828	Intermediate Similarity	NPD37	Approved
0.8153	Intermediate Similarity	NPD7028	Phase 2
0.8125	Intermediate Similarity	NPD4967	Phase 2
0.8125	Intermediate Similarity	NPD4965	Approved
0.8125	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6234	Discontinued
0.7904	Intermediate Similarity	NPD3818	Discontinued
0.7817	Intermediate Similarity	NPD1357	Approved
0.7711	Intermediate Similarity	NPD8127	Discontinued
0.7692	Intermediate Similarity	NPD4110	Phase 3
0.7692	Intermediate Similarity	NPD7228	Approved
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3705	Approved
0.7644	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5494	Approved
0.7531	Intermediate Similarity	NPD7458	Discontinued
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7074	Phase 3
0.747	Intermediate Similarity	NPD3882	Suspended
0.7468	Intermediate Similarity	NPD8166	Discontinued
0.7442	Intermediate Similarity	NPD7054	Approved
0.7432	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7473	Discontinued
0.7414	Intermediate Similarity	NPD7240	Approved
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.7401	Intermediate Similarity	NPD8434	Phase 2
0.7399	Intermediate Similarity	NPD7472	Approved
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7394	Intermediate Similarity	NPD1934	Approved
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7353	Intermediate Similarity	NPD6232	Discontinued
0.7349	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3620	Phase 2
0.7321	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6797	Phase 2
0.725	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2801	Approved
0.7241	Intermediate Similarity	NPD5844	Phase 1
0.7239	Intermediate Similarity	NPD6273	Approved
0.7237	Intermediate Similarity	NPD9494	Approved
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD7251	Discontinued
0.7215	Intermediate Similarity	NPD2935	Discontinued
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6674	Discontinued
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7179	Intermediate Similarity	NPD447	Suspended
0.7178	Intermediate Similarity	NPD2534	Approved
0.7178	Intermediate Similarity	NPD2533	Approved
0.7178	Intermediate Similarity	NPD2532	Approved
0.7171	Intermediate Similarity	NPD5647	Approved
0.7171	Intermediate Similarity	NPD2798	Approved
0.7169	Intermediate Similarity	NPD4380	Phase 2
0.7168	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6166	Phase 2
0.7153	Intermediate Similarity	NPD5283	Phase 1
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD1653	Approved
0.7101	Intermediate Similarity	NPD3817	Phase 2
0.7099	Intermediate Similarity	NPD6190	Approved
0.7095	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2800	Approved
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7066	Intermediate Similarity	NPD6599	Discontinued
0.7063	Intermediate Similarity	NPD6004	Phase 3
0.7063	Intermediate Similarity	NPD6005	Phase 3
0.7063	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2932	Approved
0.7045	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1283	Approved
0.702	Intermediate Similarity	NPD3972	Approved
0.7006	Intermediate Similarity	NPD4140	Approved
0.7006	Intermediate Similarity	NPD3226	Approved
0.6994	Remote Similarity	NPD1247	Approved
0.698	Remote Similarity	NPD1651	Approved
0.6977	Remote Similarity	NPD919	Approved
0.6975	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD230	Phase 1
0.6957	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD3787	Discontinued
0.6943	Remote Similarity	NPD8032	Phase 2
0.6941	Remote Similarity	NPD5761	Phase 2
0.6941	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD5760	Phase 2
0.6941	Remote Similarity	NPD8455	Phase 2
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1510	Phase 2
0.6933	Remote Similarity	NPD4626	Approved
0.6933	Remote Similarity	NPD3019	Approved
0.6933	Remote Similarity	NPD7003	Approved
0.6923	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6386	Approved
0.6923	Remote Similarity	NPD6385	Approved
0.6923	Remote Similarity	NPD6873	Phase 2
0.6919	Remote Similarity	NPD7075	Discontinued
0.6918	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD1607	Approved
0.6918	Remote Similarity	NPD6653	Approved
0.6915	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2424	Discontinued
0.6914	Remote Similarity	NPD3926	Phase 2
0.6909	Remote Similarity	NPD4357	Discontinued
0.6909	Remote Similarity	NPD1511	Approved
0.6908	Remote Similarity	NPD1608	Approved
0.6901	Remote Similarity	NPD5402	Approved
0.6899	Remote Similarity	NPD2979	Phase 3
0.6899	Remote Similarity	NPD1240	Approved
0.6897	Remote Similarity	NPD228	Approved
0.6894	Remote Similarity	NPD2438	Suspended
0.6882	Remote Similarity	NPD6801	Discontinued
0.6879	Remote Similarity	NPD3764	Approved
0.6879	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7097	Phase 1
0.6867	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7296	Approved
0.6859	Remote Similarity	NPD7680	Approved
0.6855	Remote Similarity	NPD5735	Approved
0.6855	Remote Similarity	NPD1933	Approved
0.6855	Remote Similarity	NPD3657	Discovery
0.6852	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5762	Approved
0.6852	Remote Similarity	NPD2344	Approved
0.6852	Remote Similarity	NPD5763	Approved
0.6852	Remote Similarity	NPD1375	Discontinued
0.6845	Remote Similarity	NPD3687	Approved
0.6845	Remote Similarity	NPD3686	Approved
0.6842	Remote Similarity	NPD2978	Approved
0.6842	Remote Similarity	NPD1091	Approved
0.6842	Remote Similarity	NPD2977	Approved
0.6842	Remote Similarity	NPD1281	Approved
0.6835	Remote Similarity	NPD6663	Approved
0.6833	Remote Similarity	NPD7038	Approved
0.6833	Remote Similarity	NPD7039	Approved
0.6832	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7033	Discontinued
0.6826	Remote Similarity	NPD1512	Approved
0.6824	Remote Similarity	NPD7157	Approved
0.6821	Remote Similarity	NPD1778	Approved
0.6818	Remote Similarity	NPD1876	Approved
0.6818	Remote Similarity	NPD8651	Approved
0.6815	Remote Similarity	NPD7095	Approved
0.6813	Remote Similarity	NPD6651	Approved
0.681	Remote Similarity	NPD1549	Phase 2
0.6807	Remote Similarity	NPD6799	Approved
0.6802	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5353	Approved
0.6798	Remote Similarity	NPD7799	Discontinued
0.6795	Remote Similarity	NPD5736	Approved
0.6795	Remote Similarity	NPD2861	Phase 2
0.6792	Remote Similarity	NPD4060	Phase 1
0.6792	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1613	Approved
0.679	Remote Similarity	NPD2796	Approved
0.679	Remote Similarity	NPD6099	Approved
0.679	Remote Similarity	NPD6100	Approved
0.6789	Remote Similarity	NPD6779	Approved
0.6789	Remote Similarity	NPD6780	Approved
0.6789	Remote Similarity	NPD6778	Approved
0.6789	Remote Similarity	NPD6777	Approved
0.6789	Remote Similarity	NPD6781	Approved
0.6789	Remote Similarity	NPD6782	Approved
0.6789	Remote Similarity	NPD6776	Approved
0.6778	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2313	Discontinued
0.6772	Remote Similarity	NPD6798	Discontinued
0.6768	Remote Similarity	NPD4236	Phase 3
0.6768	Remote Similarity	NPD4237	Approved
0.6766	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5691	Approved
0.6755	Remote Similarity	NPD5585	Approved
0.6748	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5058	Phase 3
0.6744	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6764	Approved
0.674	Remote Similarity	NPD6765	Approved
0.673	Remote Similarity	NPD6233	Phase 2
0.6727	Remote Similarity	NPD3750	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