NPASS Compound

Natural Product: NPC483060

Natural Product ID	NPC483060
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WROKLQGREWQMKH-SZCGILKCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 93 95 0 0 0 0 0 0 0 0999 V2000 3.3303 5.1144 -0.8507 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1385 4.3139 -0.4828 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2603 3.2282 0.2614 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1269 2.4053 0.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0953 0.9629 0.4722 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2561 0.4914 1.0625 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3906 0.5167 0.1171 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4682 1.5442 0.4662 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9793 1.2185 1.8255 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9083 2.1153 2.8229 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4023 1.8322 4.1835 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3153 3.4384 2.5297 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0528 -0.8377 0.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3228 -1.8016 -0.4888 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8806 -3.0811 0.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3390 -2.6948 0.1548 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1515 -3.5322 1.0616 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6115 -3.0938 0.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8013 -3.4426 2.5070 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1036 -4.8478 0.6012 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2729 -1.3310 0.4674 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2600 -1.5257 -1.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2453 -2.4822 -2.0818 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2670 -0.1106 -1.6723 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5704 -0.1368 -3.1084 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4546 -0.9912 -3.3738 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0654 0.5934 -4.2455 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4796 2.0210 -4.4118 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4889 -0.0726 -5.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8827 0.7345 -1.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4603 1.5656 -1.9076 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4087 0.2521 -0.7835 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2526 1.2487 -1.6421 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4363 -0.8377 -0.5376 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1259 -1.8684 0.4606 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3305 -2.7978 0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4164 -3.6354 -0.3950 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3793 -2.7269 1.5111 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4216 -3.7897 1.2495 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8350 -2.8493 2.9194 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8149 4.7778 -0.9559 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2782 4.5541 -0.7258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3393 6.0989 -0.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2491 5.3409 -1.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3010 3.0051 0.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2058 2.9396 0.2763 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0211 2.5850 1.7829 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8306 0.5471 1.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1136 -0.4960 1.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 1.1863 1.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0887 2.5546 0.4082 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2736 1.4107 -0.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4256 0.2754 2.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3965 0.7215 4.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6284 2.2241 4.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3775 2.2766 4.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3396 4.0644 3.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2624 3.4086 2.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9486 3.9567 1.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4356 -3.2964 1.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7449 -3.9285 -0.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7425 -2.7848 -0.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6609 -1.9777 0.7874 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0237 -3.4988 -0.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2158 -3.3422 1.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0159 -4.1593 2.8304 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7210 -3.7459 3.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5842 -2.4012 2.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7774 -4.9113 -0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0731 0.4976 -4.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6122 2.0108 -4.3651 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1652 2.7329 -3.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2453 2.3263 -5.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0523 -1.0232 -5.7069 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5763 -0.2176 -5.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2236 0.5931 -6.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5969 0.7496 -2.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6715 2.0913 -1.9310 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1801 1.3989 -1.0687 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7643 -1.3225 -1.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3589 -0.2983 -0.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2965 -2.5566 0.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1055 -1.4755 1.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8895 -1.7282 1.3780 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4307 -3.5086 1.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3815 -4.0517 0.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0663 -4.7311 1.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5160 -1.8130 3.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9595 -3.5415 2.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6435 -3.2424 3.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9168 5.5879 -1.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1468 5.0752 -0.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3045 3.9512 -1.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 8 9 1 0 9 10 2 3 10 11 1 0 10 12 1 0 7 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 16 21 1 0 14 22 1 0 22 23 2 0 22 24 1 0 24 25 1 6 25 26 2 0 25 27 1 0 27 28 1 0 27 29 1 0 24 30 1 0 30 31 2 0 24 32 1 0 32 33 1 6 32 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 38 40 1 0 2 41 1 0 32 5 1 0 30 7 1 0 21 13 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 0 4 46 1 0 4 47 1 0 5 48 1 1 6 49 1 0 6 50 1 0 8 51 1 0 8 52 1 0 9 53 1 0 11 54 1 0 11 55 1 0 11 56 1 0 12 57 1 0 12 58 1 0 12 59 1 0 15 60 1 0 15 61 1 0 16 62 1 6 18 63 1 0 18 64 1 0 18 65 1 0 19 66 1 0 19 67 1 0 19 68 1 0 20 69 1 0 27 70 1 0 28 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 29 75 1 0 29 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 35 82 1 0 35 83 1 0 38 84 1 0 39 85 1 0 39 86 1 0 39 87 1 0 40 88 1 0 40 89 1 0 40 90 1 0 41 91 1 0 41 92 1 0 41 93 1 0 M END

Standard InCHIKey	WROKLQGREWQMKH-SZCGILKCSA-N
Standard InCHI	InChI=1S/C35H52O6/c1-20(2)12-13-24-19-34(17-14-21(3)4)30-25(18-27(41-30)32(9,10)40)29(38)35(31(34)39,28(37)23(7)8)33(24,11)16-15-26(36)22(5)6/h12,14,22-24,27,40H,13,15-19H2,1-11H3/t24-,27-,33+,34+,35-/m0/s1
SMILES	CC(=CC[C@H]1C[C@]2(CC=C(C)C)C3=C(C[C@@H](C(C)(C)O)O3)C(=O)[C@@](C(=O)C(C)C)(C2=O)[C@]1(C)CCC(=O)C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.38	Volume:	622.533 ? Van der Waals volume.
Dense:	0.913	LogP:	5.933 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.415 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.27 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	20.0
TPSA:	97.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.215	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.972	Fsp³:	0.714
MCE-18:	73.7 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.813	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.04 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.042 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.518	Promiscuous compounds:	0.032

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.658	MDCK Permeability:	-4.764
Pgp-inhibitor:	0.491	Pgp-substrate:	0.003
PAMPA:	0.052 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	69.856%	Volume Distribution (VD):	0.101
Fu:	31.989% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.693
OATP1B3 inhibitor:	0.419	BCRP inhibitor:	0.005
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.97	CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.016
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.971
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	1.0
HLM stability:	0.952 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

6.409

Half-life (T1/2):

0.622

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.192
Human Hepatotoxicity (H-HT):	0.881	Drug-induced Liver Injury (DILI):	0.547
AMES Toxicity:	0.379	Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.39	Skin Sensitization:	0.95
Carcinogencity:	0.893	Eye Corrosion:	0.0
Eye Irritation:	0.068	Respiratory Toxicity:	0.539
Drug-induced Neurotoxicity:	0.262	Ototoxicity:	0.689
Hematotoxicity:	0.643	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.119
BCF:	1.824 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.687 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.301 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.854 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-015-0798-z]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.fitote.2006.01.011]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plaphy.2005.07.013]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1155/2014/609649]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32560389]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36336219]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38217369]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4391	Hypericum perforatum	Species	Hypericaceae	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	Organism Name	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

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	IC50	=	10880.0	nM	PMID[28445039]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC483060 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	20667
0.1-0.2	27996
0.2-0.3	1078
0.3-0.4	50
0.4-0.5	26
0.5-0.6	19
0.6-0.7	19
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.803	Intermediate Similarity	NPC483061
0.803	Intermediate Similarity	NPC483062
0.7846	Intermediate Similarity	NPC483059
0.6818	Remote Similarity	NPC472733
0.6818	Remote Similarity	NPC472734
0.6765	Remote Similarity	NPC471331
0.6765	Remote Similarity	NPC99657
0.6765	Remote Similarity	NPC203388
0.6522	Remote Similarity	NPC483076
0.6522	Remote Similarity	NPC483078
0.6429	Remote Similarity	NPC483064
0.6429	Remote Similarity	NPC483063
0.6389	Remote Similarity	NPC483057
0.6184	Remote Similarity	NPC47466
0.6184	Remote Similarity	NPC116274
0.6143	Remote Similarity	NPC472732
0.6143	Remote Similarity	NPC472731
0.6111	Remote Similarity	NPC471330
0.6111	Remote Similarity	NPC472687
0.6104	Remote Similarity	NPC471333
0.6104	Remote Similarity	NPC471332
0.6	Remote Similarity	NPC483058
0.5942	Remote Similarity	NPC27105
0.5857	Remote Similarity	NPC472729
0.5857	Remote Similarity	NPC472730
0.5823	Remote Similarity	NPC483077
0.5733	Remote Similarity	NPC328997
0.5733	Remote Similarity	NPC294050
0.5733	Remote Similarity	NPC610705
0.5634	Remote Similarity	NPC38885
0.5571	Remote Similarity	NPC177680
0.5571	Remote Similarity	NPC153776
0.5526	Remote Similarity	NPC483052
0.5526	Remote Similarity	NPC483051
0.5479	Remote Similarity	NPC483080
0.5479	Remote Similarity	NPC472728
0.5479	Remote Similarity	NPC472727
0.527	Remote Similarity	NPC21681
0.5256	Remote Similarity	NPC483055
0.5256	Remote Similarity	NPC483056
0.5068	Remote Similarity	NPC483067

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC483060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7227
0.1-0.2	1905
0.2-0.3	18
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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