NPASS Compound

Structure

NPC303989 OpenBabel07101719512D 25 28 0 0 1 0 0 0 0 0999 V2000 5.9033 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2723 -2.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 2.5981 -0.5000 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 4.3301 -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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 20 1 0 0 0 0 2 20 1 0 0 0 0 4 24 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 20 1 0 0 0 0 14 21 1 6 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 21 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	362.161
LogP:	5.55
LogD:	3.687
LogS:	-4.675
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	3.899
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.903
MDCK Permeability:	2.0853001842624508e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.301
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	95.6864013671875%
Volume Distribution (VD):	3.404
Pgp-substrate:	2.4893651008605957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.533
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.349
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.355
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.805
CYP3A4-inhibitor:	0.441
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	11.254
Half-life (T1/2):	0.086

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.136
Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.51
Skin Sensitization:	0.787
Carcinogencity:	0.479
Eye Corrosion:	0.005
Eye Irritation:	0.416
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC303989

Natural Product ID:	NPC303989
*Common Name:**	15,16-Dihydroswartziarboreol C
IUPAC Name:	(6aS,10aS)-11-hydroxy-12-methoxy-7,7,10a-trimethyl-1,2,5,6,6a,8,9,10-octahydronaphtho[1,2-h]isochromen-4-one
Synonyms:	15,16-Dihydroswartziarboreol C
Standard InCHIKey:	QAIIXQJPXUSTBS-QKKBWIMNSA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-20(2)9-5-10-21(3)14(20)7-6-12-15-13(8-11-25-19(15)23)18(24-4)17(22)16(12)21/h14,22H,5-11H2,1-4H3/t14-,21-/m0/s1
SMILES:	COc1c(O)c2c(c3c1CCOC3=O)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469629
PubChem CID:	11508443
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO1939	Swartzia langsdorffii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124782]
NPO27624	Swartzia simplex	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26654828]
NPO27624	Swartzia simplex	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1939	Swartzia langsdorffii	Species	Fabaceae	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug	PMID[487092]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	32.0	ug.mL-1	PMID[487092]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[487092]

☑ 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 NPC303989 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	350
0.1-0.2	1578
0.2-0.3	3382
0.3-0.4	7293
0.4-0.5	10863
0.5-0.6	5030
0.6-0.7	8159
0.7-0.8	5789
0.8-0.85	191
0.85-0.9	52
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9116	High Similarity	NPC58752
0.9073	High Similarity	NPC62051
0.9067	High Similarity	NPC124842
0.9054	High Similarity	NPC470757
0.8896	High Similarity	NPC296044
0.8896	High Similarity	NPC167098
0.8859	High Similarity	NPC474991
0.8824	High Similarity	NPC273248
0.88	High Similarity	NPC127046
0.8792	High Similarity	NPC84786
0.8758	High Similarity	NPC161778
0.875	High Similarity	NPC31132
0.8733	High Similarity	NPC191899
0.8733	High Similarity	NPC246229
0.8725	High Similarity	NPC309169
0.8725	High Similarity	NPC196941
0.8707	High Similarity	NPC475907
0.8675	High Similarity	NPC52692
0.8667	High Similarity	NPC75295
0.8662	High Similarity	NPC21046
0.8654	High Similarity	NPC143328
0.8636	High Similarity	NPC180388
0.8625	High Similarity	NPC263212
0.8618	High Similarity	NPC471852
0.8616	High Similarity	NPC29055
0.8598	High Similarity	NPC475054
0.8562	High Similarity	NPC474305
0.8562	High Similarity	NPC142654
0.8562	High Similarity	NPC102372
0.8544	High Similarity	NPC185617
0.8543	High Similarity	NPC258856
0.8535	High Similarity	NPC302258
0.8516	High Similarity	NPC218628
0.8509	High Similarity	NPC200726
0.8497	Intermediate Similarity	NPC475848
0.8497	Intermediate Similarity	NPC474306
0.8487	Intermediate Similarity	NPC169682
0.8481	Intermediate Similarity	NPC315157
0.8477	Intermediate Similarity	NPC126707
0.8477	Intermediate Similarity	NPC260152
0.8471	Intermediate Similarity	NPC25850
0.8471	Intermediate Similarity	NPC276815
0.8457	Intermediate Similarity	NPC177362
0.8452	Intermediate Similarity	NPC75377
0.8442	Intermediate Similarity	NPC300983
0.8438	Intermediate Similarity	NPC144843
0.8428	Intermediate Similarity	NPC24627
0.8418	Intermediate Similarity	NPC283301
0.8408	Intermediate Similarity	NPC16286
0.8405	Intermediate Similarity	NPC202428
0.8405	Intermediate Similarity	NPC266545
0.8397	Intermediate Similarity	NPC295646
0.8387	Intermediate Similarity	NPC50269
0.8385	Intermediate Similarity	NPC173587
0.8385	Intermediate Similarity	NPC208120
0.8354	Intermediate Similarity	NPC197751
0.8354	Intermediate Similarity	NPC472803
0.8344	Intermediate Similarity	NPC291510
0.8344	Intermediate Similarity	NPC43872
0.8344	Intermediate Similarity	NPC144801
0.8344	Intermediate Similarity	NPC238672
0.8344	Intermediate Similarity	NPC232936
0.8344	Intermediate Similarity	NPC116850
0.8344	Intermediate Similarity	NPC197188
0.8333	Intermediate Similarity	NPC477673
0.8333	Intermediate Similarity	NPC477672
0.8333	Intermediate Similarity	NPC146584
0.8333	Intermediate Similarity	NPC21016
0.8333	Intermediate Similarity	NPC471853
0.8333	Intermediate Similarity	NPC302783
0.8333	Intermediate Similarity	NPC473201
0.8323	Intermediate Similarity	NPC261322
0.8313	Intermediate Similarity	NPC47623
0.8313	Intermediate Similarity	NPC141574
0.8302	Intermediate Similarity	NPC158542
0.8301	Intermediate Similarity	NPC225351
0.8299	Intermediate Similarity	NPC293454
0.8293	Intermediate Similarity	NPC213416
0.8291	Intermediate Similarity	NPC16082
0.8291	Intermediate Similarity	NPC472835
0.8291	Intermediate Similarity	NPC82592
0.8289	Intermediate Similarity	NPC469615
0.8289	Intermediate Similarity	NPC50954
0.8282	Intermediate Similarity	NPC472452
0.8282	Intermediate Similarity	NPC472621
0.8272	Intermediate Similarity	NPC475055
0.8272	Intermediate Similarity	NPC45943
0.8272	Intermediate Similarity	NPC100420
0.8272	Intermediate Similarity	NPC25889
0.8261	Intermediate Similarity	NPC318081
0.8261	Intermediate Similarity	NPC469889
0.825	Intermediate Similarity	NPC470339
0.825	Intermediate Similarity	NPC267627
0.825	Intermediate Similarity	NPC45846
0.825	Intermediate Similarity	NPC37502
0.825	Intermediate Similarity	NPC87317
0.825	Intermediate Similarity	NPC40702
0.825	Intermediate Similarity	NPC4950
0.825	Intermediate Similarity	NPC239118
0.8239	Intermediate Similarity	NPC109765
0.8239	Intermediate Similarity	NPC227062
0.8239	Intermediate Similarity	NPC150227
0.8235	Intermediate Similarity	NPC469683
0.8235	Intermediate Similarity	NPC275278
0.8232	Intermediate Similarity	NPC472622
0.8228	Intermediate Similarity	NPC477669
0.8228	Intermediate Similarity	NPC281477
0.8224	Intermediate Similarity	NPC11314
0.8224	Intermediate Similarity	NPC192597
0.8224	Intermediate Similarity	NPC169214
0.8224	Intermediate Similarity	NPC176030
0.8224	Intermediate Similarity	NPC229218
0.8224	Intermediate Similarity	NPC184935
0.8224	Intermediate Similarity	NPC141817
0.8217	Intermediate Similarity	NPC267091
0.8217	Intermediate Similarity	NPC70320
0.8217	Intermediate Similarity	NPC228662
0.821	Intermediate Similarity	NPC22130
0.821	Intermediate Similarity	NPC116838
0.821	Intermediate Similarity	NPC215612
0.821	Intermediate Similarity	NPC474763
0.8199	Intermediate Similarity	NPC53889
0.8199	Intermediate Similarity	NPC155302
0.8199	Intermediate Similarity	NPC161947
0.8199	Intermediate Similarity	NPC472055
0.8193	Intermediate Similarity	NPC158226
0.8193	Intermediate Similarity	NPC472620
0.8188	Intermediate Similarity	NPC326847
0.8187	Intermediate Similarity	NPC247713
0.8187	Intermediate Similarity	NPC84935
0.8187	Intermediate Similarity	NPC190020
0.8187	Intermediate Similarity	NPC199463
0.8187	Intermediate Similarity	NPC77679
0.8187	Intermediate Similarity	NPC37543
0.8187	Intermediate Similarity	NPC202495
0.8182	Intermediate Similarity	NPC117911
0.8182	Intermediate Similarity	NPC163130
0.8182	Intermediate Similarity	NPC165979
0.8176	Intermediate Similarity	NPC199926
0.8176	Intermediate Similarity	NPC477671
0.8176	Intermediate Similarity	NPC213122
0.8176	Intermediate Similarity	NPC182693
0.8176	Intermediate Similarity	NPC477687
0.8171	Intermediate Similarity	NPC43319
0.8166	Intermediate Similarity	NPC473785
0.8165	Intermediate Similarity	NPC3744
0.8165	Intermediate Similarity	NPC131121
0.8165	Intermediate Similarity	NPC137125
0.8165	Intermediate Similarity	NPC164912
0.816	Intermediate Similarity	NPC220313
0.816	Intermediate Similarity	NPC236132
0.816	Intermediate Similarity	NPC477689
0.8158	Intermediate Similarity	NPC2681
0.8158	Intermediate Similarity	NPC272907
0.8155	Intermediate Similarity	NPC196771
0.8153	Intermediate Similarity	NPC243891
0.8148	Intermediate Similarity	NPC474779
0.8148	Intermediate Similarity	NPC87431
0.8148	Intermediate Similarity	NPC216916
0.8144	Intermediate Similarity	NPC316539
0.8144	Intermediate Similarity	NPC199357
0.8141	Intermediate Similarity	NPC470359
0.8141	Intermediate Similarity	NPC476394
0.8141	Intermediate Similarity	NPC98809
0.8141	Intermediate Similarity	NPC220006
0.8141	Intermediate Similarity	NPC181452
0.8137	Intermediate Similarity	NPC235448
0.8137	Intermediate Similarity	NPC85121
0.8133	Intermediate Similarity	NPC52598
0.8133	Intermediate Similarity	NPC124470
0.8133	Intermediate Similarity	NPC109827
0.8133	Intermediate Similarity	NPC477670
0.8129	Intermediate Similarity	NPC39361
0.8125	Intermediate Similarity	NPC5379
0.8125	Intermediate Similarity	NPC477675
0.8125	Intermediate Similarity	NPC77807
0.8125	Intermediate Similarity	NPC14561
0.8125	Intermediate Similarity	NPC88803
0.8125	Intermediate Similarity	NPC477674
0.8125	Intermediate Similarity	NPC104983
0.8125	Intermediate Similarity	NPC300845
0.8125	Intermediate Similarity	NPC291948
0.8125	Intermediate Similarity	NPC250436
0.8121	Intermediate Similarity	NPC218226
0.8121	Intermediate Similarity	NPC474024
0.8117	Intermediate Similarity	NPC471305
0.8117	Intermediate Similarity	NPC113397
0.811	Intermediate Similarity	NPC471788
0.811	Intermediate Similarity	NPC26386
0.811	Intermediate Similarity	NPC25361
0.811	Intermediate Similarity	NPC327652
0.8108	Intermediate Similarity	NPC49742
0.8107	Intermediate Similarity	NPC207467
0.8105	Intermediate Similarity	NPC314271
0.8105	Intermediate Similarity	NPC248068
0.8101	Intermediate Similarity	NPC306011
0.8101	Intermediate Similarity	NPC115869
0.8101	Intermediate Similarity	NPC118427
0.8101	Intermediate Similarity	NPC472838
0.8101	Intermediate Similarity	NPC144283

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 NPC303989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	1048
0.2-0.3	1953
0.3-0.4	2554
0.4-0.5	1878
0.5-0.6	913
0.6-0.7	419
0.7-0.8	82
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
0.821	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8171	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2532	Approved
0.8065	Intermediate Similarity	NPD2534	Approved
0.8065	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD1465	Phase 2
0.7919	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD4628	Phase 3
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7458	Discontinued
0.7746	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1934	Approved
0.7692	Intermediate Similarity	NPD7003	Approved
0.7692	Intermediate Similarity	NPD7228	Approved
0.7628	Intermediate Similarity	NPD6674	Discontinued
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD6959	Discontinued
0.758	Intermediate Similarity	NPD8166	Discontinued
0.7576	Intermediate Similarity	NPD4965	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7576	Intermediate Similarity	NPD4966	Approved
0.7574	Intermediate Similarity	NPD6166	Phase 2
0.7574	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2801	Approved
0.756	Intermediate Similarity	NPD5711	Approved
0.756	Intermediate Similarity	NPD5710	Approved
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7455	Intermediate Similarity	NPD7819	Suspended
0.7452	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5494	Approved
0.7434	Intermediate Similarity	NPD7985	Registered
0.743	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.741	Intermediate Similarity	NPD3817	Phase 2
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7399	Intermediate Similarity	NPD7074	Phase 3
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.7371	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3882	Suspended
0.7358	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6651	Approved
0.7346	Intermediate Similarity	NPD6273	Approved
0.7341	Intermediate Similarity	NPD7054	Approved
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.732	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7299	Intermediate Similarity	NPD7472	Approved
0.7296	Intermediate Similarity	NPD2800	Approved
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.7283	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.7246	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9494	Approved
0.7229	Intermediate Similarity	NPD7411	Suspended
0.7226	Intermediate Similarity	NPD3620	Phase 2
0.7226	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD1511	Approved
0.7216	Intermediate Similarity	NPD7240	Approved
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD2935	Discontinued
0.7215	Intermediate Similarity	NPD6100	Approved
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6190	Approved
0.7202	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7177	Discontinued
0.7159	Intermediate Similarity	NPD6797	Phase 2
0.7152	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1512	Approved
0.7119	Intermediate Similarity	NPD7251	Discontinued
0.7115	Intermediate Similarity	NPD2979	Phase 3
0.7107	Intermediate Similarity	NPD5408	Approved
0.7107	Intermediate Similarity	NPD5405	Approved
0.7107	Intermediate Similarity	NPD5406	Approved
0.7107	Intermediate Similarity	NPD5404	Approved
0.7097	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7079	Intermediate Similarity	NPD7808	Phase 3
0.7073	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7768	Phase 2
0.7047	Intermediate Similarity	NPD4626	Approved
0.7044	Intermediate Similarity	NPD2799	Discontinued
0.7039	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7435	Discontinued
0.7032	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8151	Discontinued
0.7024	Intermediate Similarity	NPD6386	Approved
0.7024	Intermediate Similarity	NPD6385	Approved
0.7022	Intermediate Similarity	NPD6559	Discontinued
0.7018	Intermediate Similarity	NPD3749	Approved
0.7018	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8434	Phase 2
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2438	Suspended
0.6995	Remote Similarity	NPD2488	Approved
0.6995	Remote Similarity	NPD2490	Approved
0.698	Remote Similarity	NPD5691	Approved
0.697	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6776	Approved
0.6968	Remote Similarity	NPD6777	Approved
0.6968	Remote Similarity	NPD6780	Approved
0.6968	Remote Similarity	NPD6781	Approved
0.6968	Remote Similarity	NPD6779	Approved
0.6968	Remote Similarity	NPD6782	Approved
0.6968	Remote Similarity	NPD6778	Approved
0.6964	Remote Similarity	NPD7028	Phase 2
0.6962	Remote Similarity	NPD447	Suspended
0.6954	Remote Similarity	NPD1281	Approved
0.6954	Remote Similarity	NPD7229	Phase 3
0.6949	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8455	Phase 2
0.6937	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2493	Approved
0.6931	Remote Similarity	NPD2494	Approved
0.6915	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4582	Approved
0.6911	Remote Similarity	NPD4583	Approved
0.6909	Remote Similarity	NPD6799	Approved
0.6909	Remote Similarity	NPD7390	Discontinued
0.6908	Remote Similarity	NPD1608	Approved
0.6901	Remote Similarity	NPD5353	Approved
0.6892	Remote Similarity	NPD7340	Approved
0.6879	Remote Similarity	NPD6798	Discontinued
0.6879	Remote Similarity	NPD2313	Discontinued
0.6879	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7783	Phase 2
0.6863	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4004	Approved
0.6859	Remote Similarity	NPD4002	Approved
0.6855	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5124	Phase 1
0.6852	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7266	Discontinued
0.6852	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7644	Approved
0.6842	Remote Similarity	NPD3452	Approved
0.6842	Remote Similarity	NPD3450	Approved
0.6835	Remote Similarity	NPD6663	Approved
0.6835	Remote Similarity	NPD8032	Phase 2
0.6833	Remote Similarity	NPD7039	Approved
0.6833	Remote Similarity	NPD7038	Approved
0.6832	Remote Similarity	NPD3748	Approved
0.6832	Remote Similarity	NPD1510	Phase 2
0.6824	Remote Similarity	NPD6873	Phase 2
0.6821	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7874	Approved
0.6821	Remote Similarity	NPD1778	Approved
0.6818	Remote Similarity	NPD5242	Approved
0.6815	Remote Similarity	NPD3027	Phase 3
0.6815	Remote Similarity	NPD7095	Approved
0.6813	Remote Similarity	NPD1607	Approved
0.681	Remote Similarity	NPD1549	Phase 2
0.6803	Remote Similarity	NPD1398	Phase 1
0.6802	Remote Similarity	NPD5402	Approved
0.68	Remote Similarity	NPD9545	Approved
0.6798	Remote Similarity	NPD3751	Discontinued
0.6797	Remote Similarity	NPD3972	Approved
0.6795	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5736	Approved
0.6792	Remote Similarity	NPD1613	Approved
0.6792	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4140	Approved
0.6791	Remote Similarity	NPD6534	Approved
0.6791	Remote Similarity	NPD6535	Approved
0.679	Remote Similarity	NPD2531	Phase 2
0.6782	Remote Similarity	NPD919	Approved
0.6772	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7698	Approved
0.6771	Remote Similarity	NPD7697	Approved
0.6771	Remote Similarity	NPD7680	Approved
0.6771	Remote Similarity	NPD7696	Phase 3
0.6771	Remote Similarity	NPD7497	Discontinued
0.677	Remote Similarity	NPD7097	Phase 1
0.6768	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4160	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