NPASS Compound

Structure

CID131905 OpenBabel06191715492D 27 30 0 0 1 0 0 0 0 0999 V2000 -5.4385 0.0837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0090 2.8100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8815 -1.5272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6807 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6808 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8402 2.4267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3631 0.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3632 2.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 3.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8402 1.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 2.9119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5222 1.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5223 2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 -0.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2035 1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2035 2.4264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8411 2.4266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 0.9704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8410 1.4556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6820 2.9118 0.0000 C 0 0 3 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 -0.8407 4.3674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.5032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6822 3.9118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0438 0.9702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0439 2.9115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8816 -0.5092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 22 2 0 0 0 0 10 18 2 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.11
Volume:	366.56
LogP:	3.255
LogD:	2.647
LogS:	-6.079
# Rotatable Bonds:	4
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	2.626
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.012
MDCK Permeability:	2.1060939616290852e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	90.1121597290039%
Volume Distribution (VD):	0.624
Pgp-substrate:	7.610224723815918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.672
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.279
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.814
CYP3A4-inhibitor:	0.434
CYP3A4-substrate:	0.599

ADMET: Excretion

Clearance (CL):	9.471
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.621
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.359
Skin Sensitization:	0.094
Carcinogencity:	0.156
Eye Corrosion:	0.003
Eye Irritation:	0.159
Respiratory Toxicity:	0.36

Download Data

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

Natural Product: NPC131905

Natural Product ID:	NPC131905
*Common Name:**	Vitrofolal C
IUPAC Name:	2,7-dihydroxy-1,9,10-trimethoxy-7H-benzo[c]fluorene-6-carbaldehyde
Synonyms:	Vitrofolal C
Standard InCHIKey:	NFTOWXYLSPBKQL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H18O6/c1-25-15-7-12-13(8-16(15)26-2)20(24)17-11(9-22)6-10-4-5-14(23)21(27-3)18(10)19(12)17/h4-9,20,23-24H,1-3H3
SMILES:	COc1cc2c(cc1OC)C(c1c2c2c(cc1C=O)ccc(c2OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515799
PubChem CID:	10361525
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	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	18

Activity Type	# Activity
Organism	18

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[482585]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[482585]

☑ 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 NPC131905 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	402
0.1-0.2	1679
0.2-0.3	3353
0.3-0.4	9366
0.4-0.5	9563
0.5-0.6	3499
0.6-0.7	7395
0.7-0.8	7151
0.8-0.85	257
0.85-0.9	25
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC213401
0.9161	High Similarity	NPC137125
0.9161	High Similarity	NPC3744
0.9145	High Similarity	NPC39361
0.9097	High Similarity	NPC70320
0.9013	High Similarity	NPC300603
0.9013	High Similarity	NPC91694
0.8931	High Similarity	NPC143328
0.8766	High Similarity	NPC275278
0.8734	High Similarity	NPC75377
0.8726	High Similarity	NPC261322
0.8704	High Similarity	NPC141574
0.8696	High Similarity	NPC296044
0.8696	High Similarity	NPC167098
0.8688	High Similarity	NPC180901
0.8688	High Similarity	NPC300757
0.8679	High Similarity	NPC131121
0.8616	High Similarity	NPC302783
0.8616	High Similarity	NPC473201
0.8581	High Similarity	NPC50954
0.8554	High Similarity	NPC43065
0.8537	High Similarity	NPC469889
0.8519	High Similarity	NPC279605
0.8519	High Similarity	NPC109765
0.8509	High Similarity	NPC62051
0.8506	High Similarity	NPC82336
0.8506	High Similarity	NPC78987
0.8503	High Similarity	NPC177362
0.85	High Similarity	NPC78505
0.85	High Similarity	NPC472838
0.85	High Similarity	NPC306011
0.8494	Intermediate Similarity	NPC26386
0.8485	Intermediate Similarity	NPC116838
0.8485	Intermediate Similarity	NPC22130
0.8471	Intermediate Similarity	NPC193377
0.8466	Intermediate Similarity	NPC202495
0.8452	Intermediate Similarity	NPC266545
0.8452	Intermediate Similarity	NPC202428
0.8447	Intermediate Similarity	NPC164912
0.8443	Intermediate Similarity	NPC263212
0.8443	Intermediate Similarity	NPC200726
0.8405	Intermediate Similarity	NPC478223
0.8397	Intermediate Similarity	NPC141817
0.8397	Intermediate Similarity	NPC192597
0.8397	Intermediate Similarity	NPC229218
0.8397	Intermediate Similarity	NPC176030
0.8397	Intermediate Similarity	NPC169214
0.8395	Intermediate Similarity	NPC474000
0.8385	Intermediate Similarity	NPC118427
0.8385	Intermediate Similarity	NPC124842
0.8354	Intermediate Similarity	NPC9370
0.8354	Intermediate Similarity	NPC287495
0.8354	Intermediate Similarity	NPC37543
0.8354	Intermediate Similarity	NPC178976
0.8354	Intermediate Similarity	NPC199463
0.8343	Intermediate Similarity	NPC117911
0.8333	Intermediate Similarity	NPC180388
0.8323	Intermediate Similarity	NPC58310
0.8323	Intermediate Similarity	NPC295977
0.8323	Intermediate Similarity	NPC477689
0.8313	Intermediate Similarity	NPC216916
0.8313	Intermediate Similarity	NPC311740
0.8303	Intermediate Similarity	NPC245891
0.8303	Intermediate Similarity	NPC104876
0.8301	Intermediate Similarity	NPC152209
0.8293	Intermediate Similarity	NPC77807
0.8293	Intermediate Similarity	NPC5379
0.8293	Intermediate Similarity	NPC14561
0.8291	Intermediate Similarity	NPC196941
0.8291	Intermediate Similarity	NPC309169
0.8284	Intermediate Similarity	NPC186392
0.8282	Intermediate Similarity	NPC303950
0.8282	Intermediate Similarity	NPC475770
0.8272	Intermediate Similarity	NPC118332
0.8272	Intermediate Similarity	NPC144283
0.8272	Intermediate Similarity	NPC267091
0.8266	Intermediate Similarity	NPC47191
0.8263	Intermediate Similarity	NPC198796
0.8263	Intermediate Similarity	NPC473445
0.8263	Intermediate Similarity	NPC42797
0.8261	Intermediate Similarity	NPC300983
0.8261	Intermediate Similarity	NPC142654
0.8253	Intermediate Similarity	NPC84571
0.8253	Intermediate Similarity	NPC472962
0.8253	Intermediate Similarity	NPC472961
0.825	Intermediate Similarity	NPC58373
0.825	Intermediate Similarity	NPC52692
0.8246	Intermediate Similarity	NPC312006
0.8246	Intermediate Similarity	NPC471920
0.8246	Intermediate Similarity	NPC20114
0.8246	Intermediate Similarity	NPC129930
0.8246	Intermediate Similarity	NPC114550
0.8246	Intermediate Similarity	NPC292712
0.8246	Intermediate Similarity	NPC471922
0.8246	Intermediate Similarity	NPC471921
0.8246	Intermediate Similarity	NPC474075
0.8239	Intermediate Similarity	NPC160777
0.8239	Intermediate Similarity	NPC225351
0.8239	Intermediate Similarity	NPC73416
0.8232	Intermediate Similarity	NPC268008
0.8228	Intermediate Similarity	NPC93433
0.8228	Intermediate Similarity	NPC264706
0.8228	Intermediate Similarity	NPC46161
0.8228	Intermediate Similarity	NPC16353
0.8228	Intermediate Similarity	NPC239608
0.8228	Intermediate Similarity	NPC284881
0.8228	Intermediate Similarity	NPC474444
0.8225	Intermediate Similarity	NPC174734
0.8225	Intermediate Similarity	NPC255787
0.8225	Intermediate Similarity	NPC474042
0.8224	Intermediate Similarity	NPC228843
0.8214	Intermediate Similarity	NPC101769
0.8214	Intermediate Similarity	NPC45943
0.8214	Intermediate Similarity	NPC291977
0.821	Intermediate Similarity	NPC31132
0.821	Intermediate Similarity	NPC243891
0.821	Intermediate Similarity	NPC225854
0.8208	Intermediate Similarity	NPC196771
0.8204	Intermediate Similarity	NPC478222
0.8198	Intermediate Similarity	NPC184624
0.8198	Intermediate Similarity	NPC199357
0.8193	Intermediate Similarity	NPC228501
0.8187	Intermediate Similarity	NPC131866
0.8187	Intermediate Similarity	NPC58752
0.8187	Intermediate Similarity	NPC52598
0.8182	Intermediate Similarity	NPC288353
0.8182	Intermediate Similarity	NPC115123
0.8182	Intermediate Similarity	NPC239113
0.8176	Intermediate Similarity	NPC311912
0.8176	Intermediate Similarity	NPC469521
0.8171	Intermediate Similarity	NPC93552
0.8171	Intermediate Similarity	NPC107109
0.8166	Intermediate Similarity	NPC41689
0.816	Intermediate Similarity	NPC272566
0.8155	Intermediate Similarity	NPC476247
0.8155	Intermediate Similarity	NPC144843
0.8148	Intermediate Similarity	NPC472837
0.8144	Intermediate Similarity	NPC155302
0.8144	Intermediate Similarity	NPC24627
0.8144	Intermediate Similarity	NPC161947
0.8144	Intermediate Similarity	NPC21046
0.8144	Intermediate Similarity	NPC36217
0.8141	Intermediate Similarity	NPC141368
0.814	Intermediate Similarity	NPC4200
0.814	Intermediate Similarity	NPC469506
0.8137	Intermediate Similarity	NPC470757
0.8137	Intermediate Similarity	NPC236166
0.8133	Intermediate Similarity	NPC302258
0.8129	Intermediate Similarity	NPC88557
0.8125	Intermediate Similarity	NPC157133
0.8125	Intermediate Similarity	NPC474799
0.8125	Intermediate Similarity	NPC68441
0.8121	Intermediate Similarity	NPC472835
0.8118	Intermediate Similarity	NPC43319
0.811	Intermediate Similarity	NPC295646
0.811	Intermediate Similarity	NPC323626
0.811	Intermediate Similarity	NPC470769
0.811	Intermediate Similarity	NPC60211
0.811	Intermediate Similarity	NPC149889
0.811	Intermediate Similarity	NPC65591
0.811	Intermediate Similarity	NPC312338
0.811	Intermediate Similarity	NPC178574
0.811	Intermediate Similarity	NPC324233
0.811	Intermediate Similarity	NPC180944
0.8107	Intermediate Similarity	NPC223006
0.8107	Intermediate Similarity	NPC173729
0.8107	Intermediate Similarity	NPC197168
0.8107	Intermediate Similarity	NPC270837
0.8107	Intermediate Similarity	NPC124038
0.8107	Intermediate Similarity	NPC134047
0.8107	Intermediate Similarity	NPC272750
0.8095	Intermediate Similarity	NPC87431
0.8095	Intermediate Similarity	NPC96031
0.8092	Intermediate Similarity	NPC143483
0.8092	Intermediate Similarity	NPC316539
0.8089	Intermediate Similarity	NPC1268
0.8089	Intermediate Similarity	NPC308768
0.8089	Intermediate Similarity	NPC12668
0.8086	Intermediate Similarity	NPC476394
0.8086	Intermediate Similarity	NPC98809
0.8084	Intermediate Similarity	NPC472299
0.8084	Intermediate Similarity	NPC45846
0.8084	Intermediate Similarity	NPC477692
0.8084	Intermediate Similarity	NPC125713
0.8084	Intermediate Similarity	NPC85121
0.8084	Intermediate Similarity	NPC324736
0.8081	Intermediate Similarity	NPC313304
0.8075	Intermediate Similarity	NPC476359
0.8075	Intermediate Similarity	NPC476338
0.807	Intermediate Similarity	NPC474024
0.807	Intermediate Similarity	NPC218226
0.807	Intermediate Similarity	NPC247973
0.8063	Intermediate Similarity	NPC207732
0.8063	Intermediate Similarity	NPC472836
0.8063	Intermediate Similarity	NPC105213
0.8061	Intermediate Similarity	NPC473365
0.8061	Intermediate Similarity	NPC54179
0.8061	Intermediate Similarity	NPC25127
0.8059	Intermediate Similarity	NPC474301
0.8059	Intermediate Similarity	NPC326520

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 NPC131905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	969
0.2-0.3	1543
0.3-0.4	2693
0.4-0.5	1938
0.5-0.6	1038
0.6-0.7	493
0.7-0.8	105
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
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8235	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3620	Phase 2
0.7871	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7784	Intermediate Similarity	NPD37	Approved
0.7784	Intermediate Similarity	NPD1934	Approved
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7746	Intermediate Similarity	NPD6166	Phase 2
0.7746	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6273	Approved
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8127	Discontinued
0.7662	Intermediate Similarity	NPD9494	Approved
0.7657	Intermediate Similarity	NPD3818	Discontinued
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD7003	Approved
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD3882	Suspended
0.7647	Intermediate Similarity	NPD4965	Approved
0.7633	Intermediate Similarity	NPD2801	Approved
0.7605	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6959	Discontinued
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.756	Intermediate Similarity	NPD4380	Phase 2
0.7557	Intermediate Similarity	NPD7228	Approved
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3027	Phase 3
0.743	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5761	Phase 2
0.7427	Intermediate Similarity	NPD5760	Phase 2
0.7407	Intermediate Similarity	NPD2935	Discontinued
0.7405	Intermediate Similarity	NPD3764	Approved
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7074	Phase 3
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2532	Approved
0.7362	Intermediate Similarity	NPD5763	Approved
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD5762	Approved
0.7353	Intermediate Similarity	NPD7028	Phase 2
0.7318	Intermediate Similarity	NPD7054	Approved
0.7312	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1511	Approved
0.7301	Intermediate Similarity	NPD5404	Approved
0.7301	Intermediate Similarity	NPD5405	Approved
0.7301	Intermediate Similarity	NPD5406	Approved
0.7301	Intermediate Similarity	NPD5408	Approved
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD7472	Approved
0.7278	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1876	Approved
0.7244	Intermediate Similarity	NPD1283	Approved
0.7241	Intermediate Similarity	NPD7768	Phase 2
0.7225	Intermediate Similarity	NPD7819	Suspended
0.7219	Intermediate Similarity	NPD1512	Approved
0.7205	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1613	Approved
0.72	Intermediate Similarity	NPD7075	Discontinued
0.7198	Intermediate Similarity	NPD7039	Approved
0.7198	Intermediate Similarity	NPD7038	Approved
0.7197	Intermediate Similarity	NPD1470	Approved
0.719	Intermediate Similarity	NPD1651	Approved
0.7184	Intermediate Similarity	NPD3817	Phase 2
0.7184	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD1247	Approved
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7177	Discontinued
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5735	Approved
0.7158	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7134	Intermediate Similarity	NPD1510	Phase 2
0.7134	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3750	Approved
0.7126	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8166	Discontinued
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.7117	Intermediate Similarity	NPD1607	Approved
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7104	Intermediate Similarity	NPD7251	Discontinued
0.7104	Intermediate Similarity	NPD7240	Approved
0.7102	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7099	Intermediate Similarity	NPD4140	Approved
0.7099	Intermediate Similarity	NPD2979	Phase 3
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7097	Intermediate Similarity	NPD8434	Phase 2
0.7097	Intermediate Similarity	NPD8150	Discontinued
0.7091	Intermediate Similarity	NPD2438	Suspended
0.7089	Intermediate Similarity	NPD3094	Phase 2
0.7086	Intermediate Similarity	NPD5978	Approved
0.7086	Intermediate Similarity	NPD5977	Approved
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7069	Intermediate Similarity	NPD6801	Discontinued
0.7065	Intermediate Similarity	NPD7808	Phase 3
0.7062	Intermediate Similarity	NPD919	Approved
0.7059	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7055	Intermediate Similarity	NPD3657	Discovery
0.7051	Intermediate Similarity	NPD1281	Approved
0.7051	Intermediate Similarity	NPD1201	Approved
0.7051	Intermediate Similarity	NPD3092	Approved
0.7048	Intermediate Similarity	NPD2344	Approved
0.7048	Intermediate Similarity	NPD6002	Phase 3
0.7048	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6004	Phase 3
0.7048	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6005	Phase 3
0.7047	Intermediate Similarity	NPD6777	Approved
0.7047	Intermediate Similarity	NPD6780	Approved
0.7047	Intermediate Similarity	NPD6776	Approved
0.7047	Intermediate Similarity	NPD6779	Approved
0.7047	Intermediate Similarity	NPD6778	Approved
0.7047	Intermediate Similarity	NPD6781	Approved
0.7047	Intermediate Similarity	NPD6782	Approved
0.7037	Intermediate Similarity	NPD6663	Approved
0.7032	Intermediate Similarity	NPD4626	Approved
0.703	Intermediate Similarity	NPD2799	Discontinued
0.7024	Intermediate Similarity	NPD4110	Phase 3
0.7024	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8151	Discontinued
0.7011	Intermediate Similarity	NPD7411	Suspended
0.7011	Intermediate Similarity	NPD6764	Approved
0.7011	Intermediate Similarity	NPD6765	Approved
0.7006	Intermediate Similarity	NPD1549	Phase 2
0.7006	Intermediate Similarity	NPD3749	Approved
0.7	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD3926	Phase 2
0.6994	Remote Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD943	Approved
0.6989	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5402	Approved
0.6988	Remote Similarity	NPD1551	Phase 2
0.6978	Remote Similarity	NPD3751	Discontinued
0.6974	Remote Similarity	NPD6823	Phase 2
0.6961	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6599	Discontinued
0.6951	Remote Similarity	NPD447	Suspended
0.6948	Remote Similarity	NPD5536	Phase 2
0.6946	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7266	Discontinued
0.6946	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7229	Phase 3
0.694	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7435	Discontinued
0.6937	Remote Similarity	NPD4624	Approved
0.6923	Remote Similarity	NPD3019	Approved
0.6914	Remote Similarity	NPD6386	Approved
0.6914	Remote Similarity	NPD6385	Approved
0.6914	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4625	Phase 3
0.6905	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7870	Phase 2
0.6904	Remote Similarity	NPD7871	Phase 2
0.6903	Remote Similarity	NPD3091	Approved
0.6899	Remote Similarity	NPD3972	Approved
0.6898	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD2491	Approved
0.6888	Remote Similarity	NPD3057	Approved
0.6886	Remote Similarity	NPD2796	Approved
0.6882	Remote Similarity	NPD2309	Approved
0.6871	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2313	Discontinued
0.6866	Remote Similarity	NPD7783	Phase 2
0.6866	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6784	Approved
0.6862	Remote Similarity	NPD6785	Approved
0.6859	Remote Similarity	NPD5691	Approved
0.6855	Remote Similarity	NPD5327	Phase 3
0.6855	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7696	Phase 3
0.6853	Remote Similarity	NPD7698	Approved
0.6853	Remote Similarity	NPD7697	Approved
0.6853	Remote Similarity	NPD7680	Approved
0.6851	Remote Similarity	NPD3787	Discontinued
0.6851	Remote Similarity	NPD5710	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